*4.10. (3ß) 28-(1,5-Diazocan-1-yl)-28-oxours-12-en-3-yl Acetate (15)*

Following GP 2 from 3-*O*-acetyl-ursolic acid (10, 500 mg, 1.0 mmol), followed by chromatography (silica gel, CHCl3/MeOH (2% → 10%), compound **15** (413 mg, 69%) was obtained as an off-white solid; m.p. = 232–235 ◦C (decomp.); Rf = 0.37 (CHCl3/MeOH, 95:5); [*α*] 20 *<sup>D</sup>* = + 0.45◦ (*c* 0.088, CHCl3); IR (ATR): *ν* = 2942*m*, 1731*m*, 1627*m*, 1456*m*, 1370*s*, 1245*s*, 1026*s*, 750*s*, 662*m* cm−1; 1H NMR (400 MHz, CDCl3): δ = 5.18–5.13 (*m*, 1H, 12-H), 4.46–4.39 (*m*, 1H, 3-H), 3.74–3.01 (*m*, 8H, 33-H, 35-H, 36-H, 38-H), 2.39 (*d*, *J* = 11.3 Hz, 1H, 18-H), 1.99 (*s*, 3H, 32-H), 1.88–1.82 (*m*, 2H, 11-H), 1.74–1.67 (*m*, 1H, 20-H), 1.73–1.05 (*m*, 23H, 2-H, 6-H, 15-H, 16-H, 21-H, 7-H, 9-H, 22-H, 1Ha, 19-H, 34-H, 37-H), 1.02 (*s*, 3H, 27-H), 0.99–0.95 (m, 1H, 1Hb), 0.92 (*s*, 3H, 23-H), 0.88 (*s*, 3H, 30-H), 0.86 (*s*, 3H, 25-H), 0.81 (*s*, 3H, 29-H), 0.80 (*s*, 3H, 24-H), 0.77-0.74 (*m*, 1H, 5-H), 0.72 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 174.9 (C-28), 171.0 (C-31), 125.3 (C-12), 80.9 (C-3), 55.2 (C-5), 55.0 (C-18), 48.7 (C-33, C-35, C-36, C-38), 48. 6 (C-17), 47.7 (C-9), 43.4 (C- 8), 43.5 (C-14), 39.4 (C-19), 38.7 (C-20), 38.6 (C-1), 37.6 (C-4), 37.0 (C-10), 33.9 (C-22), 32.9 (C-7), 30.6 (C-21), 28.1 (C-23), 27.3 (C-34, C-37), 27.0 (C-15), 26.4 (C-16), 23,4 (C-27), 23.5 (C-2), 23.3 (C-11), 21.2 (C-32), 21.0 (C-30), 18.3 (C-6), 16.7 (C-29), 16.39 (C-26), 15.62 (C-24), 15.40 (C-25) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 596.2 (100%, [M+H]+); analysis calcd. for C38H62N2O3 (594.93): C 76.72, H 10.50, N 4.71; found: C 76.58, H 10.76, N 4.49.

#### *4.11. (3ß) 28-(1,5-Diazocan-1-yl)-28-oxolup-20(29)-en-3-yl Acetate (16)*

Following GP 2 from 3-*O*-acetyl-betulinic acid (11, 500 mg, 1.0 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH (10% → 50%), compound **16** (430 mg, 72%) was obtained as a colorless solid; m.p. 223–234 ◦C (decomp.); Rf = 0.43 (CHCl3/MeOH, 9:1); [*α*] 20 *<sup>D</sup>* = −8.0◦ (*c* 0.064, CHCl3); IR (ATR): *ν* = 3408*w*, 2942*m*, 1731*m*, 1632*s*, 1455*m*, 1373*s*, 1246*s*, 1195*m*, 1026*m*, 979*m*, 882*m*, 730*s* cm−1; 1H NMR (400 MHz, CDCl3): δ = 4.68 (*m*, 1H, 29-Ha), 4.56–4.53 (*m*, 1H, 29-Hb), 4.42 (*dd*, J = 10.1, 6.2 Hz, 1H, 3-H), 4.02–3.19 (*m*, 8H, 33-H, 35-H, 36-H, 38-H), 2.85 (*m*, 2H, 13-H, 19-H), 2.13–2.08 (*m*, 1H, 16-Ha), 2.00 (*s*, 3H, 32-H), 1.96–1.93 (*m*, 1H, 22-Ha), 1.78–1.74 (*m*, 1H, 21-Ha1.65–1.63 (*m*, 5H, 1-Ha, 12-Ha, 30-H), 1.60–1.05 (*m*, 2-H, 16-Hb, 18-H, 6-Ha, 7-H, 21-H, 11-H, 22-Hb,34-H, 37-H, 9-H, 15-H), 0.96–0.94 (*m*, 1H, 1-Hb), 0.92 (*s*, 3H, 27-H), 0.90–0.89 (*m*, 1H, 12-Hb), 0.87 (*s*, 3H, 25-H), 0.80 (*s*, 3H,m 24-H), 0.79 (*s*, 3H, 23-H), 0.76–0.74 (*m*, 1H, 5-H), 0.72 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 175.4 (C-28), 171.0 (C-31), 150.8 (C-20), 109.4 (C-29), 80.9 (C-3), 55.5 (C-5), 55.2 (C-33, C-35, C-36, C-38), 55.0 (C-17), 52.9 (C-18), 50.7 (C-9), 45.6 (C-19), 42.0 (C-14), 40.7 (C-8), 38.8 (C-4), 38.4 (C-1), 37.8 (C-10), 37.1 (C-7), 36.9 (C-13), 36.1 (C-22), 34.3 (C-34, C-37), 32.3 (C-16), 31.4 (C-21), 30.1 (C-15), 25.5 (C-23), 23.7 (C-12), 23.7 (C-2), 21.3 (C-32), 21.1 (C-11), 19.7 (C-30), 18.1 (C-6), 16.4 (C-24), 16.2 (C-25), 16.0 (C-26), 14.6 (C-27) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 596.1 (100%, [M+H]+); analysis calcd. for C38H62N2O3 (594.93): C 76.72, H 10.50, N 4.71; found: C 76.46, H 10.77, N 4.53.

### *4.12. (3ß)28-(1,5-Diazocan-1-yl)-30-nor-20,28-dioxolup-3-yl-acetate (17)*

Following GP 2 from 3-*O*-acetyl-platanic acid (12, 500 mg, 1.0 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH (10% → 50%), compound **17** (425 mg, 70%) was obtained as a colorless solid; m.p. = 210–214 ◦C (decomp.); Rf = 0.44 (CHCl3/MeOH, 9:1); [*α*] 20 *<sup>D</sup>* = −26.6◦ (*c* 0.028, CHCl3); IR (ATR): *ν* = 3396*w*, 2942*m*, 2866*m*, 1731*m*, 1626*s*, 1466*m*, 1411*m*, 1369*m*, 1197*s*, 1245*m*, 1120*m*, 1025*m*, 978*m* cm<sup>−</sup>1; 1H NMR (400 MHz, CDCl3): δ = 4.39 (*dd*, *J* = 10.6, 5.5 Hz, 1H, 3-H), 3.78–3.06 (*m*, 9H, 19-H, 32-H, 34-H, 35-H, 37-H), 2.66–2.56 (*m*, 1H, 13-H), 2.10 (*s*, 3H, 29-H), 2.08–1.98 (*m*, 2H, 16-Ha, 18-H), 1.97 (*s*, 3H, 31-H), 1.94–1.90 (*m*, 1H, 22-Ha), 1.82–1.76 (*m*, 1H, 21-Ha), 1.70–1.05 (*m*, 19H, 1-Ha, 16-Hb, 2-H, 22-Hb, 21-Hb, 6-Ha, 11-Ha, 7-H, 6Hb, 9-H, 15-H, 11-Hb, 33-H, 36-H), 0.98–0.95 (*m*, 2H, 12-H), 0.92 (*s*, 3H, 27-H), 0.91–0.85 (*m*, 1H, 1-Hb), 0.83 (*s*, 3H, 24-H), 0.79–0.77 (*m*, 6H, 23-H, 25-H), 0.76 (*s*, 3H, 26-H), 0.72–0.71 (*m*, 1H, 5-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 212.5 (C-20), 175.3 (C-28), 170.9 (C-30), 80.8 (C-3), 55.4 (C-5), 55.1 (C-32, C-34, C-35, C-37), 52.7 (C-18), 50.6 (C-9), 49.9 (C-19), 46.1 (C-17), 41.8 (C-8), 40.6 (C-14), 38.3 (C-1), 37.7 (C-4), 37.1 (C-10), 35.9 (C-13), 35.8 (C-22), 34.1 (C-7), 31.8 (C-16), 30.3 (C-29), 30.0 (C-15), 28.8 (C-21), 27.9 (C-23), 27.3 (C-12), 23.6 (C-2), 21.3 (C-31), 21.1 (C-11), 18.1 (C-6), 16.4 (C-26), 16.2 (C-25), 15.9 (C-24), 14.6 (C-27) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 597.3 (100%, [M+H+); analysis calcd. for C37H60N2O4 (596.90): C 74.45, H 10.13, N 4.69; found: C 74.21, H 10.32, N 4.43.

#### *4.13. (2α,3ß,4α)28-(1,5-Diazocan-1-yl)-28-oxours-12-ene-2,3,23-triyl Triacetate (18)*

Following GP 2 from 2,3,24-tri-*O*-acetyl-asiatic acid (13, 400 mg, 0.8 mmol), followed by chromatography [silica gel, CHCl3/MeOH (2% → 50%)], compound **18** (425 mg, 74%) was obtained as colorless solid; m.p. = 187–190 ◦C (decomp.); Rf = 0.38 (CHCl3/MeOH, 9:1); [*α*] 20 *<sup>D</sup>* = −30.2◦ (*c* 0.015, CHCl3); IR (ATR): *ν* = 2925*w,* 1741*s*, 1623*w*, 1368*m*, 1231*s*, 1042*m*, 748*w* cm−1; 1H NMR (400 MHz, CDCl3): δ = 5.22–5.17 (*m*, 1H, 12-H), 5.14–5.08 (*m*, 1H, 2-H), 5.04–5.01 (*m*, 1H, 3-H), 3.80 (*m*, 1H, 23-Ha), 3.51 (*m*, 1H, 23-Hb), 3.32–2.67 (*m*, 8H, 37-H, 39-H, 40-H, 42-H), 2.40–2.34 (*m*, 1H, 18-H), 2.03 (*s*, 3H, 36-H), 2.02–2.00 (*m*, 1H, 1-Ha), 1.97 (*s*, 3H, 34-H), 1.92 (*s*, 3H, 32-H), 1.88–1.69 (*m*, 5H, 11-H, 16-H 22-Ha), 1.60–1.45 (*m*, 4H, 22-Hb, 9-H, 21-Ha, 7-Ha), 1.53–1.45 (*m*, 2H, 16-Ha, 16-Hb), 1.33–1.14 (*m*, 10H, 19-H, 5-H, 21-Hb, 7-Hb, 15-H, 38-H, 41-H), 1.11–1.09 (*m*, 1H, 1-Hb), 1.05 (*s*, 3H, 27-H), 1.02 (s, 3H, 25-H), 0.99-0.96 (*m*, 1H, 20-H), 0.91 (*s*, 3H, 30-H), 0.84 (*s*, 3H, 24-H), 0.82 (*s*, 3H, 29-H), 0.70 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 176.8 (C-28), 170.8 (C-35), 170.3 (C-33), 170.3 (C-31), 138.7 (C-13), 124.9 (C-12), 74.8 (C-3), 69.8 (C-2), 65.2 (C-23), 55.6 (C-18), 47.6 (C-9), 47.5 (C-5), 46.1 (C-37, C-39, C-40, C-42), 43.7 (C-1), 42.3 (C-14), 41.9 (C-4), 39.5 (C-8), 39.3 (C-19), 38.5 (C-20), 37.8 (C-10), 34.8 (C-22), 34.7 (C-7), 31.9 (C-21), 29.6 (C-15), 23.3 (C-11), 23.2 (C-16), 22.6 (C-38, C-41), 21.2 (C-30), 21.0 (C-36), 20.8 (C-32), 20.7 (C-34), 17.8 (C-6), 17.4 (C-27), 17.3 (C-29), 17.1 (C-25), 13.9 (C-26), 8.7 (C-24) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 711.8 (100%, [M+H+); analysis calcd. for C42H66N2O7 (711.00): C 70.95, H 9.36, N 3.94; found: C 70.69, H 9.51, N 3.75.

*4.14. (3ß)-3-Acetyloxy-28-(5-{2-[3,6-bis(diethylamino)xanthen-10-ium-9-yl]benzoyl}-1,5 diazocan-1-yl)-28-oxoolean-12-ene Chloride (19)*

Following GP 3 from **14** (150 mg, 0.14 mmol) and rhodamine B (100 mg, 0.2 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 10% → 40%), **19** (100 mg, 72%) was obtained as a pink solid; m.p. = 211–216 ◦C; Rf = 0.44 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 562 nm (4.53); IR (ATR): *ν* = 2926*m*, 2605*w*, 2498*w*, 1729*w*, 1587*s*, 1466*s*, 1412*s*, 1336, 1245*s*, 1180*s*, 1132*m*, 1073*s,* 1009*m*, 921*w*, 748*m*, 683*m* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.67–7.57 (*m*, 2H, 43-H, 44-H), 7.53–7.47 (*m*, 1H, 42-H), 7.34–7.26 (*m*, 3H, 45-H, 48-H), 7.14–6.65 (*m*, 4H, 49-H, 51-H), 5.25–5.15 (*m*, 1H, 12-H), 4.51–4.40 (*m*, 1H, 3-H), 3.78–3.20 (*m*, 16H, 33-H, 35-H, 36-H, 38-H, 53-H), 3.05–2.95 (*m*, 1H, 18-H), 2.07–2.02 (*m*, 1H, 16-Ha), 2.01–1.99 (*m*, 3H, 32-H), 1.89–1.81 (*m*, 2H, 11-H), 1.67–1.37 (*m*, 14H, 19-Ha, 1-Ha, 2-H, 9-H, 6-Ha, 15-Ha, 22-Ha, 21-Ha, 6-Hb, 34-H, 37-H), 1.30–1.24 (*m*, 12H, 54-H), 1.23–1.13 (*m*, 6H, 16-Hb, 7-H 22-Hb, 21-Hb, 19-Hb,), 1.08 (*s*, 3H, 27-H), 0.99 (*m*, 2H, 1-Hb, 15-Hb), 0.87 (*s*, 3H, 25-H), 0.86 (*s*, 3H, 29-H), 0.84 (*s*, 3H, 30-H), 0.82 (*s*, 3H, 23-H), 0.80 (*s*, 3H, 24-H), 0.79–0.76 (*m*, 1H, 5-H), 0.68 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 170.9 (C-28, C-31), 168.7 (C-39), 157.7 (C-52), 155.8 (C-46), 155.7 (C-50), 145.4 (C-13), 136.6 (C-41), 132.5 (C-49), 130.4 (C-40), 130.1 (C-42), 130.0 (C-44), 129.4 (C-43), 127.7 (C-45), 121.2 (C-129, 113.9 (C-47), 96.1 (C-48, C-51), 80.9 (C-3), 55.3 (C-5), 48.4 (C-17), 47.6 (C-9), 46.6 (C-19), 46.2 (C-53), 46.1 (C-33, C-35, C-36, C-38), 44.7 (C-18), 42.0 (C-14), 39.1 (C-8), 38.0 (C-1), 37.6 (C-4), 37.0 (C-10), 34.1 (C-21), 32.9 (C-30), 32.8 (C-22), 30.3 (C-20), 29.6 (C-7), 28.0 (C-15), 28.0 (C-23), 25.8 (C-27), 24.0 (C-29), 23.5 (C-2), 23.3 (C-11), 22.6 (C-16), 21.3 (C-32), 18.2 (C-6), 17.2 (C-26), 16.6 (C-24), 15.4 (C-25), 12.7 (C-54) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1021.4 (98%, [M-Cl]+); analysis calcd. for C66H91N4O5Cl (1055.93): C 75.07, H 8.69, N 5.31; found: C 74.87, H 8.82, N 5.08.

#### *4.15. (3ß)-3-Acetyloxy-28-(5-{2-[3,6-bis(diethylamino)xanthen-10-ium-9-yl]benzoyl}-1,5 diazocan-1-yl)-28-oxours-12-ene Chloride (20)*

Following GP 3 from **15** (150 mg, 0.14 mmol) and rhodamine B (100 mg, 0.2 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 10% → 40%), **20** (94 mg, 63%) was obtained as a pink solid; m.p. = 194–197 ◦C (decomp.); Rf = 0.41 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 560 nm (5.54); IR (ATR): *ν* = 2932*w*, 1726*w*, 1586*s*, 1465*m*, 1411*s*, 1335*s*, 1272*m*, 1245*s*, 1179*s*, 1132*m*, 1073*m*, 1009*m*, 921*m,* 823*w*, 746*m*, 683*m*, 663*m*, 498*m* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.68–7.56 (*m*, 2H, 43-H, 44-H), 7.53–7.49 (*m*, 1H, 42-H), 7.32–7.25 (*m*, 3H, 45-H, 48-H), 7.18–6.54 (*m*, 4H, 49-H, 51-H), 5.24–5.11 (*m*, 1H, 12-H), 4.50–4.39 (*m*, 1H, 3-H), 4.12–2.76 (*m*, 16H, 33-H, 35-H, 36-H, 38-H,53-H), 2.43–2.33 (*m*, 1H, 18-H), 2.09–2.07 (*m*, 1H, 16-Ha), 2.00 (*s*, 3H, 32-H), 1.91–1.84 (*m*, 2H, 11-H), 1.77–1.36 (*m*, 14H, 1-Ha, 2-H, 21-Ha, 6-Ha, 9-H, 22-Ha, 19-H, 6-Hb, 16-Hb, 34-H, 37-H), 1.29 (*t*, J = 7.1 Hz, 12H, 54-H), 1.23 (*m*, 6H, 7-H, 15-H, 21-Hb, 22-Hb), 1.03 (s, 4H, 1-Hb, 27-H), 0.96–0.93 (*m*, 1H, 20-H), 0.90 (*s*, 3H, 29-H), 0.88 (*s*, 3H, 25-H), 0.83 (*s*, 3H, 30-H), 0.82 (*s*, 3H, 23-H), 0.81 (*s*, 3H, 24-H), 0.77–0.75 (*m*, 1H, 5-H), 0.69 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 170.9 (C-28), 157.7 (C-31), 157.7 (C-39), 155.8 (C-50), 155.7 (C-46) 155.6 (C-52), 136.6 (C-40), 132.9 (C-48), 130.1 (C-44), 130.0 (C-42), 129.4 (C-43), 127.0 (C-45), 125.0 (C-12), 113.9 (C-47), 96.2 (C-49, C-51), 80.9 (C-3), 55.3 (C-18), 55.3 (C-5), 49.4 (C-17), 47.5 (C-9), 46.2 (C-33, C-35, C-36, C-38), 46.1 (C-53), 42.4 (C-14), 39.6 (C-19), 39.3 (C-8), 38.6 (C-20), 38.2 (C-1), 37.6 (C-4), 36.9 (C-10), 32.7 (C-22), 31.9 (C-7), 30.5 (C-21), 29.6 (C-15), 29.3 (C-16), 28.0 (C-23), 23.2 (C-2), 23.1 (C-11), 23.0 (C-27), 18.1 (C-6), 17.4 (C-30), 17.2 (C-26), 16.7 (C-24), 15.5 (C-25), 12.7 (C-54) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1020.4 (100%, [M-Cl]+); analysis calcd. For C66H91N4O5Cl (1055.93): C 75.07, H 8.69, N 5.31; found: C 74.83, H 8.91, N 5.03.

#### *4.16. (3ß)-3-Acetyloxy-28-(5-{2-[3,6-bis(diethylamino)xanthen-10-ium-9-yl]benzoyl}-1,5 diazocan-1-yl)-28-oxolup-20(29)-ene Chloride (21)*

Following GP 3 from **16** (300 mg, 0.5 mmol) and rhodamine B (200 mg, 0.4 mmol), followed by chromatography (silica gel, CHCl3/MeOH, 9:1), **21** (3536 mg, 69%) was obtained as a pink solid; m.p. = 212–218 ◦C; Rf = 0.49 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 562 nm (4.43); IR (ATR): *ν* = 2936*w*, 1730*w*, 1587*s*, 1465*m*, 1411*s*, 1335*s*, 1244*s*, 1179*s*, 1132*m*, 1073*m*, 978*w,* 921*w*, 684*m* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.52–7.47 (*m*, 2H, 43-H, 44-H), 7.43–7.37 (*m*, 1H, 42-H), 7.22–6.99 (*m*, 3H, 45-H, 48-H), 6.97–6.71 (*m*, 2H, 49-H), 6.64–6.57 (*m*, 2H, 51-H), 4.58–4.50 (*m*, 1H, 29-Ha), 4.42–4.37 (*m*, 1H, 29-Hb), 4.30 (*m*, 1H, 3-H), 3.73–2.93 (*m*, 16H, 33-H, 35-H, 36-H, 38-H, 53-H), 2.83–2.68 (*m*, 2H, 19-H, 13-H), 2.00–1.94 (*m*, 1H, 16-Ha), 1.87 (*s*, 3H, 32-H), 1.83–1.54 (*m*, 4H, 22-Ha, 15-H, 21-Ha), 1.53–1.51 (*m*, 2H, 12-Ha, 1-Ha), 1.50 (*s*, 3H, 30-H), 1.47–1.42 (*m*, 2H, 2-H), 1.41–1.36 (*m*, 1H, 18-H), 1.35–1.29 (*m*, 2H, 16-Ha, 6-Ha), 1.28–1.12 (*m*, 21H, 11-Ha, 6-Hb, 7-H, 22-Hb, 54-H, 34-H, 37-H), 1.11–1.09 (*m*, 2H, 11-Hb, 9-H, 21-Hb), 0.83–0.74 (*m*, 8H, 1-Hb, 12-Hb, 23-H, 27-H), 0.69–0.65 (*m*, 9H, 26-H, 25-H, 24-H), 0.63–0.59 (*m*, 1H, 5-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 170.8 (C-28), 168.5 (C-39), 167.6 (C-31), 157.6 (C-50), 155.6 (C-46), 155.5 (C-52), 151.2 (C-20), 136.4 (C-40), 132.3 (C-41), 130.8 (C-48), 130.0 (C-43), 129.4 (C-42), 128.6 (C-45), 127.0 (C-44), 114.6 (C-49), 113.6 (C-47), 108.9 (C-29), 96.0 (C-51), 80.8 (C-3), 55.2 (C-5), 55.1 (C-38, C-36, C-35, C-33), 53.0 (C-18), 50.6 (C-9), 46.1 (C-53), 45.8 (C-19), 41.9 (C-17), 40.6 (C-8), 40.6 (C-14), 38.3 (C-1), 37.7 (C-10), 37.0 (C-4), 36.8 (C-13), 36.0 (C-22), 34.2 (C-7), 32.0 (C-16), 31.3 (C-21), 30.2 (C-34, C-37), 29.8 (C-15), 27.8 (C-24), 25.5 (C-12), 25.4 (C-37, C-34), 23.6 (C-2), 21.2 (C-32), 21.0 (C-11), 19.6 (C-30), 18.1 (C-6), 16.1 (C-25), 15.9 (C-26), 14.6 (C-23), 14.5 (C-27), 12.6 (C-54) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1020.5 (100%, [M-Cl]+); analysis calcd. for C66H91N4O5Cl (1055.93): C 75.07, H 8.69, N 5.31; found: C 74.86, H 8.90, N 5.09.

### *4.17. (3ß)-3-Acetyloxy-28-(5-{2-[3,6-bis(diethylamino)xanthen-10-ium-9-yl]benzoyl}-1,5 diazocan-1-yl)-28-oxolup-20-oxo Chloride (22)*

Following GP 3 from **17** (300 mg, 0.50 mmol) and rhodamine B (300 mg, 0.6 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 9:1), **22** (350 mg, 69%) was obtained as a pink solid; m.p. = 198–201 ◦C; Rf = 0.51 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 558 nm (4.73); IR (ATR): *ν* = 2934*w*, 1721*m*, 1585*s*, 1410*m*, 1466*s*, 1334*s*, 1272*s*, 1245*s*, 1131*s*, 1072*s*, 1009*s*, 977*m*, 921*m*, 823*m*, 755*m*, 682*s* cm<sup>−</sup>1; 1H NMR (400 MHz, CDCl3): δ = 7.67–7.57 (*m*, 2H, 42-H, 43-H), 7.53–7.47 (*m*, 1H, 41-H), 7.35–7.27 (*m*, 3H, 44-H, 47-H), 7.11–6.64 (*m*, 4H, 48-H, 50-H), 4.46–4.36 (*m*, 1H, 3-H), 3.88–3.20 (*m*, 16H, 32-H, 34-H, 35-H, 37-H, 52-H), 3.16–3.05 (*m*, 1H, 18-H), 2.76–2.51 (*m*, 1H, 13-H), 2.11–2.04 (*m*, 4H, 16-Ha, 29-H), 1.98 (*s*, 4H, 19-H, 31-H), 1.78 (*s*, 2H, 21-Ha, 22-Ha), 1.62–1.48 (*m*, 4H, 1-Ha, 2-H, 16-Ha), 1.42 (*m*, 7H, 6-Ha, 22-Hb, 21-Hb, 11-H, 7-Ha, 6-Hb), 1.28 (*t*, *J* = 6.8 Hz, 14H, 7-Hb, 9-H, 53-H), 1.23–1.04 (*m*, 6H, 33-H, 36-H, 15-H), 0.94 (*s*, 2H, 12-H), 0.91 (*s*, 4H, 1-Hb, 24-H), 0.82 (*s*, 3H, 27-H), 0.78 (*m*, 10H, 23-H, 25-H, 26-H, 5-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 212.8 (C-20), 170.9 (C-28, C-30, C- 38), 157.7 (C-49), 155.7 (C-45), 155.6 (C-51), 136.6 (C-39), 136.5 (C-40), 132.4 (C-47), 130.1 (C-42), 129.7 (C-43), 129.4 (C-44), 127.1 (C-41), 114.5 (C-48), 113.7 (C-46), 96.2 (C-50), 80.8 (C-3), 55.4 (C-5), 55.3 (C-32, C-34, C-35, C-37), 53.0 (C-19), 50.6 (C-9), 50.3 (C-18), 49.5 (C-17), 46.2 (C-52), 41.9 (C-14), 40.6 (C-8), 38.3 (C-1), 37.7 (C-4), 37.1 (C-10), 35.8 (C-13), 35.6 (C-22), 34.2 (C-7), 31.6 (C-16), 30.1 (C-29), 29.9 (C-15), 28.8 (C-21), 27.9 (C-23), 27.4 (C-12), 23.6 (C-2), 22.6 (C-33, C-36), 21.1 (C-11), 18.1 (C-6), 16.4 (C-25), 16.2 (C-26), 14.7 (C-24), 14.0 (C-27), 12.7 (C-53) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1022.4 (100%, [M-Cl]+); analysis calcd. for C65H89N4O6Cl (1057.90): C 73.80, H 8.48, N 5.30; found: C 73.55, H 8.67, N 5.07.

#### *4.18. (2α,3ß,4α)2,3,23-Tris (acetyloxy)-28-(5-{2-[3,6-bis(diethylamino)xanthen-10-ium-9 yl]benzoyl}-1,5-diazocan-1-yl)-28-oxours-12-en Chloride (23)*

Following GP 3 from **18** (300 mg, 0.4 mmol) and rhodamine B (250 mg, 0.5 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 9:1), **23** (184 mg, 60%) was obtained as a pink solid; m.p. = 225 ◦C; Rf = 0.44 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 562 nm (4.50); IR (ATR): *ν* = 2927*w*, 1793*m*, 1587*s*, 1467*m*, 1411*m*, 1336*s*, 1244*s*, 1179*s*, 1042*m*, 921*w*, 684*m*, 436*w* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.66–7.57 (*m*, 2H, 47-H, 48-H), 7.52–7.47 (*m*, 1H, 46-H), 7.27-7.20 (m, 49-H, 52-H), 7.17–6.63 (*m*, 4H, 53-H, 55-H), 5.20–5.00 (*m*, 3H, 12-H, 2-H, 3-H), 3.82–3.76 (*m*, 1H, 23-Ha), 3.73–2.93 (*m*, 17H, 37-H, 39-H, 40-H, 42-H, 57-H, 23-Hb), 2.44–2.33 (*m*, 1H, 18-H), 2.04 (*s*, 3H, 34-H), 2.02–1.99 (*m*, 1H, 1-Ha), 1.97 (*s*, 3H, 36-H), 1.93 (*s*, 3H, 32-H), 1.90–1.32 (*m*, 15H, 11-H, 9-H, 15-H, 16-Ha, 21-Ha, 22-Ha, 20-H, 38-H, 41-H, 6-H), 1.28 (*t*, *J* = 7.1 Hz, 13H, 5-H, 58-H), 1.25–1.10 (*m*, 5H, 7-H, 16-Hb, 21-Hb, 22-Hb), 1.09–1.07 (*m*, 1H, 1-Hb), 1.04 (*s*, 3H, 30-H), 1.01 (*s*, 3H, 27-H), 0.97–0.92 (*m*, 1H, 19-H), 0.88 (*s*, 3H, 29-H), 0.84 (*s*, 3H, 25-H), 0.81 (*s*, 3H, 26-H), 0.69 (*s*, 3H, 24-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 176.2 (C-43), 170.8 (C-35), 170.4 (C-31, C-33), 170.3 (C-28), 157.7 (C-54), 155.7 (C-56), 155.6 (C-50), 138.6 (C-13), 136.6 (C-45), 132.3 (C-52), 130.1 (C-47), 130.0 (C-49), 129.3 (C-48), 127.2 (C-46), 125.9 (C-12), 113.9 (C-51), 96.2 (C-53, C-55), 74.8 (C-3), 69.9 (C-2), 65.3 (C-23), 55.5 (C-18), 53.4 (C-37, C-39, C-40, C-42), 47.6 (C-5), 47.5 (C-9), 46.2 (C-57), 46.1 (C-17), 43.7 (C-1), 42.5 (C-4), 41.9 (C-14), 38.9 (C-8), 38.7 (C-20), 38.6 (C-19), 37.8 (C-10), 32.6 (C-22), 30.5 (C-21), 29.6 (C-7), 28.4 (C-15), 23.4 (C-27), 23.3 (C-11), 21.2 (C-29), 21.0 (C-32), 20.8 (C-36), 20.7 (C-34), 17.8 (C-6), 17.4 (C-26), 17.2 (C-30), 17.0 (C-24), 13.9 (C-25), 12.6 (C-58) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1036.5 (100%, [M-Cl]+); analysis calcd. for C70H95N4O9Cl (1172.00): C 71.74, H 8.17, N 4.78; found: C 71.49, H 8.35, N 4.47.

#### *4.19. 3β-Acetyloxy-28-[4-[3-(2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-pyrido [3,2,1-ij]pyrido[1",2",3":1',8']quinolino[6',5':5,6]pyrano[2,3-f ]quinolin-4-ium-9-yl)benzoyl]1,5-diazocan-1-yl]-28-oxo-olean-12-en Chloride (24)*

Following GP 3 from **14** (100 mg, 0.14 mmol) and rhodamine 101 (200 mg, 0.4 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 10% → 50%), **24** (114 mg, 75%) was obtained as a pink solid; m.p. = 205–210 ◦C; Rf = 0.41 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 580 nm (4.23); IR (ATR): *ν* = 2942*w,* 1727*m*, 1595*s*, 1493*m*, 1459*m*, 1362*m*, 1295*s*, 1196*s*, 1035*m*, 746*m,* 420*m* cm<sup>−</sup>1; 1H NMR (400 MHz, CDCl3): δ = 7.81–7.61 (*m*, 2H, 45-H), 7.54–7.43 (*m*, 1H, 42-H), 7.29 (*s*, 1H, 44-H), 6.86–6.47 (*m*, 2H, 48-H), 5.27–5.21 (*m*, 1H, 12-H), 4.51–4.44 (*m*, 1H, 3-H), 3.79–3.15 (*m*, 16H, 33-H, 35-H, 36-H, 38-H, 52-H, 57-H), 3.09–2.90 (*m*, 5H, 18-H, 55-H,), 2.76–2.47 (*m*, 4H, 50-H), 2.15–2.06 (*m*, 4H, 56-H), 2.03 (*s*, 3H, 32-H), 1.97 (*s*, 5H, 16-Ha, 51-H), 1.85 (*s*, 2H, 11-H), 1.70–1.15 (*m*, 20H, 19-Ha, 21-H, 2-H, 1-Ha, 9-H, 6-Ha, 7-Ha, 6-Hb, 22-Ha, 7-Hb, 15-H, 22-Hb, 19-Hb, 34-H, 37-H), 1.12 (*s*, 3H, 30-H), 1.07–0.97 (*m*, 2H, 1-Hb, 16-Hb), 0.91 (*s*, 3H, 25-H), 0.90 (*s*, 3H, 27-H), 0.88 (*s*, 3H, 29-H), 0.85 (*s*, 3H, 23-H), 0.83 (*s*, 3H, 24-H), 0.81–0.79 (*m*, 1H, 5-H), 0.72 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 171.0 (C-28, C-31, C-39), 164.1 (C-53), 152.0 (C-46), 139.9 (C-58), 134.6 (C-41), 131.0 (C-40), 130.5 (C-44), 129.4 (C-45, C-42), 126.9 (C-43), 125.9 (C-48), 123.5 (C-47), 121.4 (C-12), 113.0 (C-49), 105.3 (C-54), 81.0 (C-3), 55.4 (C-5), 51.1 (C-33, C-35, C-36, C-38), 50.5 (C-52, C-57), 48.2 (C-17), 47.6 (C-9), 46.6 (C-19), 43.7 (C-18), 43.3 (C-14), 39.1 (C-8), 38.1 (C-1), 37.7 (C-4), 37.0 (C-10), 33.9 (C-22), 33.0 (C-29), 32.9 (C-7), 30.5 (C-20), 30.3 (C-21), 29.7 (C-15), 28.0 (C-23), 27.8 (C-16), 27.6 (C-50), 25.8 (C-30), 24.1 (C-27), 23.5 (C-2), 23.4 (C-11), 21.3 (C-32), 20.6 (C-51), 19.9 (C-55), 19.7 (C-56), 18.2 (C-6), 17.2 (C-26), 16.7 (C-24), 15.4 (C-25) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1068.6 (100%, [M-Cl]+); analysis calcd. For C70H91N4O5Cl (1103.97): C 76.16, H 8.31, N 5.08; found: C 75.81, H 8.52, N 4.89.

#### *4.20. 3β-Acetyloxy-28-[4-[3-(2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-pyrido[3,2,1 ij]pyrido[1",2",3":1',8']quinolino[6',5':5,6]pyrano[2,3-f]uinoline-4-ium-9-yl)benzoyl]1,5 diazocan-1-yl]-28-oxo-urs-12-en Chloride (25)*

Following GP 3 from **15** (150 mg, 0.2 mmol) and rhodamine 101 (150 mg, 0.3 mmol), followed by chromatography (silica gel, ethyl acetate/MeOH, 10% → 50%), **25** (94 mg, 62%) was obtained as a pink solid; m.p. = 199–202 ◦C; Rf = 0.43 (CHCl3:Methanol, 9:1); UV-Vis (CHCl3): λmax (log ε) = 571 nm (3.94); IR (ATR): *ν* = 3388*w,* 2925*m*, 1728*m*, 1597*s*, 1495*m*, 1459*m*, 1362*s*, 1297*s*, 1246*s*, 1195*s*, 1100*s*, 1024*s,* 421*s* cm−1; 1H NMR (400 MHz, CDCl3): δ = 8.36–8.06 (*m*, 1H, 43-H), 7.75–7.63 (*m*, 2H, 42-H, 45-H), 7.24–7.11 (*m*, 1H, 44-H), 6.81–6.50 (*m*, 2H, 48-H), 5.26–5.16 (*m*, 1H, 12-H), 4.49–4.43 (*m*, 1H, 3-H), 3.71–3.21 (*m*, 16H, 33-H, 35-H, 36-H, 38-H, 52-H, 57-H), 3.17–2.90 (*m*, 4H, 55-H), 2.81–2.57 (*m*, 4H, 50-H), 2.23–2.06 (*m*, 4H, 56-H), 2.01 (*s*, 3H, 32-H), 1.98–1.84 (*m*, 6H, 51-H, 11-Ha, 16-Ha), 1.66–1.19 (*m*, 22H, 1-Ha, 11-Hb, 21-Ha, 6-Ha, 22-Ha, 19-H, 6-Hb, 21-Hb, 22-Hb, 2-H, 15-H, 7-H, 16-Hb, 18-H, 34-H, 37-H), 1.13–1.10 (*m*, 3H, 29-H), 1.05 (*s*, 3H, 27-H), 1.04–0.99 (*m*, 2H, 1-Hb, 20-H), 0.92 (*s*, 3H, 24-H), 0.85 (*s*, 3H, 25-H), 0.83 (*s*, 3H, 23-H), 0.82 (*s*, 3H, 30-H), 0.79–0.77 (*m*, 1H, 5-H), 0.72 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 171.0 (C-28), 169.3 (C-31, C-39), 151.2 (C-53), 150.9 (C-46), 135.2 (C-58), 132.3 (C-42), 131.3 (C-43), 130.2 (C-45), 129.1 (C-44), 127.1 (C-48), 125.1 (C-12), 112.6 (C-49), 111.6 (C-47), 105.6 (C-54), 80.9 (C-3), 55.3 (C-5), 47.7 (C-33, C-35, C-36, C-38), 47.5 (C-18), 47.5 (C-9), 45.3 (C-17), 43.3 (C-52, C-57), 41.7 (C-14), 39.6 (C-8), 39.5 (C-19), 38.6 (C-20), 38.2 (C-1), 37.7 (C-4), 36.9 (C-10), 33.1 (C-22), 31.9 (C-7), 30.5 (C-21), 29.7 (C-15), 28.0 (C-16), 27.8 (C-23), 27.5 (C-50), 25.0 (C-34, C-37), 23.5 (C-11), 23.4 (C-27), 23.3 (C-51), 22.6 (C-2), 21.3 (C-32), 19.9 (C-55), 19.7 (C-56), 18.7 (C-29), 18.1 (C-6), 17.3 (C-30), 16.7 (C-26), 15.5 (C-24), 14.1 (C-25) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1068.4 (100%, [M-Cl]+); analysis calcd. for C70H91N4O5Cl (1103.97): C 76.16, H 8.31, N 5.08; found: C 75.87, H 8.59, N 4.83.

#### *4.21. 3β-Acetyloxy-28-[4-[3-(2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-pyrido[3,2,1-ij] pyrido[1",2",3":1',8']quinolino[6',5':5,6]pyrano[2,3-f]quinolin-4-ium-9-yl)benzoyl] 1,5-diazocan-1-yl]-28-oxo-lup-20(29)-en Chloride (26)*

Following GP 3 from **16** (200 mg, 0.14 mmol) and rhodamine 101 (200 mg, 0.4 mmol), followed by chromatography (silica gel, CHCl3/MeOH, 9:1), **26** (103 mg, 68%) was obtained as a pink solid; m.p. = 203–206 ◦C; Rf = 0.44 (CHCl3/MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 578 nm (4.33); IR (ATR): *ν* = 2931*w,* 1721*w*, 1595*s*, 1493*s*, 1361*m*, 1294*s*, 1246*s*, 1180*s*, 1035*s*, 746*m*, 622*m*, 421*s* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.68–7.53 (*m*, 2H, 43-H, 45-H), 7.52–7.45 (*m*, 1H, 42-H), 7.31–7.26 (*m*, 1H, 44-H), 6.76–6.59 (*m*, 2H, 48-H), 4.70–4.62 (*m*, 1H, 29-Ha), 4.54–4.49 (*m*, 1H, 29-Hb), 4.44–4.38 (*m*, 1H, 3-H), 3.81–3.02 (*m*, 16H, 33-H, 35-H, 36-H, 38-H, 52-H, 57-H), 3.00–2.89 (*m*, 4H, 55-H), 2.88–2.72 (*m*, 2H, 13-H, 18-H), 2.71–2.51 (*m*, 4H, 50-H), 2.16–2.01 (*m*, 5H, 16-Ha, 56-H), 1.99 (*s*, 3H, 32-H), 1.96–1.87 (*m*, 5H, 21-Ha, 51-H), 1.85–1.74 (*m*, 2H, 15-Ha, 22-Ha), 1.70–1.66 (*m*, 1H, 12-Ha), 1.62 (*s*, 4H, 1-Ha, 30-H), 1.60–1.53 (*m*, 2H, 2-H), 1.50–1.47 (*m*, 1H, 9-H), 1.47–1.40 (*m*, 2H, 6-Ha, 16-Hb), 1.36–1.06 (*m*, 13H, 11-Ha, 21-Hb, 6-Hb, 7-H, 15-Hb, 19-H, 22-Hb, 11-Hb, 34-H, 37-H), 0.94 (*s*, 2H, 1-Hb, 12-Hb), 0.90 (*s*, 3H, 24-H), 0.86 (*s*, 3H, 25-H), 0.81 (*s*, 3H, 27-H), 0.79 (*s*, 3H, 23-H), 0.73 (*s*, 3H, 26-H), 0.70–0.59 (*m*, 1H, 5-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 170.9 (C-28), 168.8 (C-31, C-39), 151.9 (C-53), 151.3 (C-46), 151.2 (C-20), 138.4 (C-40, C-41), 136.5 (C-58), 130.4 (C-44), 129.4 (C-45, C-42), 127.1 (C-48), 127.0 (C-43) 123.5 (C-47), 113.1 (C-49), 109.1 (C-29), 105.3 (C-54), 81.0 (C-3), 55.5 (C-5), 53.1 (C-9), 52.9, 50.9 (C-33, C-35, C-36, C-38), 50.7 (C-19), 50.5 (C-52, C-57), 49.4 (C-17), 45.9 (C-13), 42.0 (C-14), 40.7 (C-14), 40.6 (C-8), 38.4 (C-1), 37.8 (C-4), 37.1 (C-10), 36.9 (C-18), 36.1 (C-21), 34.3 (C-7), 32.1 (C-16), 31.4 (C-22), 29.9 (C-15), 27.9 (C-23), 27.5 (C-50), 25.5 (C-12), 23.7 (C-2), 22.6 (C-34, C-37), 21.3 (C-32), 21.1 (C-11), 20.6 (C-51), 19.8 (C-55), 19.6 (C-56), 18.7 (C-30), 18.2 (C-6), 16.5 (C-25), 16.4 (C-26), 14.7 (C-24), 14.6 (C-27) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1067.2 (100%, [M-Cl]+); analysis calcd. for C70H91N4O5Cl (1103.97): C 76.16, H 8.31, N 5.08; found: C 75.98, H 8.52, N 4.83.

*4.22. 3β-Acetyloxy-28-[4-[3-(2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15H-pyrido[3,2,1-ij] pyrido[1",2",3":1',8']quinolino[6',5':5,6]pyrano[2,3-f]quinolin-4-ium-9-yl)benzoyl] 1,5-diazocan-1-yl]-30-nor-20,28-dioxo-lup-20(29)-en Chloride (27)*

Following GP 3 from **17** (200 mg, 0.3 mmol) and rhodamine 101 (100 mg, 0.2 mmol), followed by chromatography (silica gel, CHCl3/MeOH, 9:1), **27** (132 mg, 60%) was obtained as a pink solid; m.p. = 208–210 ◦C; Rf = 0.49 (CHCl3:MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 577 nm (4.66); IR (ATR): *ν* = 3350*w,* 1596*s*, 1195*s*, 1298*s*, 1197*s*, 1138*s* cm−1; 1H NMR (400 MHz, CDCl3): δ = 7.63–7.52 (*m*, 2H, 41-H, 44-H), 7.50–7.43 (*m*, 1H, 42-H), 7.24–7.20 (*m*, 1H, 43-H), 6.72–6.59 (*m*, 2H, 47-H), 4.42–4.33 (*m*, 1H, 3-H), 3.86–3.01 (*m*, 17H, 18-H, 32-H, 34-H, 35-H, 37H, 49-H, 51-H), 2.97–2.85 (*m*, 4H, 54-H), 2.76–2.54 (*m*, 4H, 49-H), 2.52–2.43 (*m*, 1H, 13-H), 2.18–2.06 (*m*, 4H, 21-Hb, 29-H), 2.07–1.99 (*m*, 4H, 55-H), 1.96 (*s*, 4H, 19-H, 31-H), 1.94–1.64 (*m*, 7H, 50-H, 22-Ha, 16-Ha, 15-Ha), 1.60–1.14 (*m*, 18H, 1-Ha, 2-H, 21-Hb, 22-Hb, 6-Ha, 16-Hb, 11-Ha, 7-H, 6-Hb, 11-Hb, 15-Hb), 1.08–0.96 (*m*, 3H, 1-Hb, 12-H), 0.90 (*s*, 3H, 24-H), 0.85 (*s*, 3H, 25-H), 0.80 (*s*, 3H, 27-H), 0.76 (*s*, 3H, 23-H), 0.71 (s, 3H, 26-H), 0.69–0.65 (m, 1H, 5-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 213.2 (C-20), 170.9 (C-28, C-30, C-38), 151.9 (C-52), 151.2 (C-45), 136.6 (C-57), 136.3 (C-39, C-40), 130.4 (C-43), 129.4 (C-41, C-44), 126.8 (C-42), 126.7 (C-47), 123.5 (C-46), 113.0 (C-48), 105.2 (C-53), 80.8 (C-3), 55.4 (C-5), 53.0 (C-19), 50.9 (C-32, C-34, C-35, C-37), 50.6 (C-9), 50.4 (C-51, C-56), 50.3 (C-18), 49.8 (C-17), 44.1 (C-13), 41.8 (C-14), 40.6 (C-8), 38.3 (C-1), 37.7 (C-10), 37.1 (C-4), 35.8 (C-22), 34.2 (C-7), 31.8 (C-21), 30.1 (C-29), 29.9 (C-15), 28.8 (C-16), 27.9 (C-23), 27.5 (C-49), 27.3 (C-12), 23.6 (C-2), 22.6 (C-33, C-36), 21.2 (C-31), 21.1 (C-11), 20.6 (C-50), 19.9 (C-54), 19.6 (C-55), 18.1

(C-6), 16.4 (C-26), 15.9 (C-25), 14.7 (C-24), 14.0 (C-27) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1070 (100%, [M-Cl]+); analysis calcd. for C69H89N4O6Cl (1105.94): C 74.94, H 8.11, N 5.07; found: C 74.73, H 8.35, N 4.81.

*4.23. (2α,3ß,4α)2,3,23-Tris(acetoxy)-28-[4-[3-(2,3,6,7,12,13,16,17-octahydro-1H,5H,11H,15Hpyrido[3,2,1-ij]pyrido[1",2",3":1',8']quinolino[6',5':5,6]pyrano[2,3-f]quinolin-4-ium-9 yl)benzoyl]1,5-diazocan-1-yl]-28-oxo-olean-12-en Chloride (28)*

Following GP 3 from **18** (200 mg, 0.3 mmol) and rhodamine 101 (200 mg, 0.4 mmol), followed by chromatography (silica gel, CHCl3/MeOH, 9:1), **28** (232 mg, 64%) was obtained as a pink solid; m.p. = 193–196 ◦C; Rf = 0.45 (CHCl3:MeOH, 9:1); UV-Vis (CHCl3): λmax (log ε) = 578 nm (4.50); IR (ATR): *ν* = 2924*w,* 1739*w*, 1594*s*, 1493*s*, 1459*m*, 1361*m*, 1293*s*, 1195*s*, 1180*s*, 1090*s*, 1035*s*, 729*m,* 622*m*, 421*s* cm−1; 1H NMR (400 MHz, CDCl3): δ =7.67–7.58 (*m*, 2H, 47-H, 49-H), 7.52–7.48 (*m*, 1H, 46-H), 7.29–7.27 (*m*, 1H, 48-H), 6.77–6.65 (*m*, 2H, 52-H), 5.17–5.03 (*m*, 3H, 12-H, 2-H, 3-H), 3.83–3.79 (*m*, 1H, 23-Ha), 3.60–3.16 (*m*, 17H, 23-Hb, 37-H, 39-H, 40-H, 42-H, 56-H, 61-H), 3.00–2.94 (*m*, 4H, 59-H), 2.77–2.63 (*m*, 4H, 54-H), 2.46–2.36 (*m*, 1H, 18-H), 2.07 (*s*, 4H, 60-H), 2.06 (*s*, 3H, 36-H), 2.04–2.01 (*m*, 1H, 1-Ha), 1.99 (*s*, 3H, 34-H), 1.95 (*s*, 7H, 32-H, 55-H), 1.91–1.86 (*m*, 2H, 11-H), 1.60–1.57 (*m*, 1H, 9-H), 1.46–1.42 (*m*, 2H, 21-Ha, 22-Hb), 1.35–1.30 (*m*, 4H, 6-H, 19-H, 5-H), 1.26–1.22 (*m*, 12H, 16-Ha, 38-H, 41-H, 22-Hb, 7-H, 15-H, 21-Hb, 16-Hb), 1.11–1.09 (*m*, 1H, 1-Hb), 1.04 (*s*, 3H, 24-H), 0.98–0.94 (*m*, 1H, 20-H), 0.91 (*s*, 3H, 29-H), 0.85 (*s*, 3H, 25-H), 0.83 (*s*, 3H, 27-H), 0.82 (*s*, 3H, 30-H), 0.72 (*s*, 3H, 26-H) ppm; 13C NMR (101 MHz, CDCl3): δ = 176.3 (C-28), 170.8 (C-35, C-43), 170.4 (C-33), 170.3 (C-31), 152.0 (C-57), 151.3 (C-50), 139.1 (C-62), 136.6 (C-44), 130.3 (C-45), 129.6 (C-48), 129.2 (C-46) 129.1 (C-49), 127.0 (C-47, C-52), 124.5 (C-12), 123.4 (C-51), 113.0 (C-53), 105.2 (C-58), 74.9 (C-3), 69.9 (C-2), 65.3 (C-23), 55.6 (C-18), 51.0 (C-34, C-37, C-40, C-42), 50.5 (C-56, C-61), 47.7 (C-5), 47.5 (C-9), 46.2 (C-17), 43.7 (C-1), 41.9 (C-4, C-14), 39.5 (C-19), 38.6 (C-20), 37.8 (C-10), 32.6 (C-22), 31.9 (C-7), 30.6 (C-21), 29.7 (C-15), 29.6 (C-16), 27.6 (C-54), 23.3 (C-11), 22.6 (C-38, C-41), 22.6 (C-27), 21.2 (C-29), 21.0 (C-32), 20.8 (C-36), 20.7 (C-34), 20.6 (C-55), 19.9 (C-59), 19.7 (C-60), 17.9 (C-6), 17.4 (C-30), 17.1 (C-24), 17.0 (C-26), 14.1 (C-25) ppm; MS (ESI, MeOH/CHCl3, 4:1): *m*/*z* = 1084.3 (100%, [M-Cl]+); analysis calcd. for C74H95N4O9Cl (1220.04): C 72.85, H 7.85, N 4.59; found: C 72.63, H 8.01, N 4.39.
