3.1.21. (3*S*,4*S*)-7-(aminomethyl)-4-methoxy-5,8-bis(methoxymethoxy)-3-pentylisochroman-1-one (**14a**)

To a solution of diMOM azide derivative **13a** (3.3 mg, 7.8 μmol) in MeOH (0.78 mL) was added Et3N (0.10 mL, 7.35 mmol) and Pd/C (1.6 mg, 1.5 μmol) at room temperature. After stirring for 1 h at the same temperature, the mixture was filtered, and the filtrate was concentrated under reduced pressure. The residue was purified with PTLC (MeOH:CH2Cl2 = 1:9) to give diMOM amine derivative **14a** (2.0 mg, 65%) as brown oil. 1H-NMR (400 MHz, CDCl3) δ 7.49 (1H, s), 5.26 (2H, s), 5.16 (1H, d, *J* = 7.2 Hz), 5.07 (1H, d, *J* = 6.8 Hz), 4.61 (1H, d, *J* = 1.2 Hz), 4.27 (1H, ddd, *J* = 1.2, 6.0, 7.6 Hz), 4.00 (2H, s), 3.61 (3H, s), 3.50 (3H, s), 3.32 (3H, s), 2.59 (1H, br-s), 2.03 (1H, m), 1.82 (1H, m), 1.57 (1H, m), 1.43 (1H, m), 1.40-1.25 (1H, overlapped), 0.91 (3H, t, *J* = 6.8 Hz); 13C-NMR (125 MHz, CDCl3) δ 162.6, 152.6, 150.5, 128.1, 120.0, 119.0, 102.4, 95.4, 81.2, 68.5, 57.9, 57.2, 56.8, 42.5, 32.0, 30.9, 30.0, 25.2, 22.9, 14.4.; IR (KBr) 2957, 2925, 2857, 2827, 1726, 1470, 1153, 1005 cm<sup>−</sup>1; HRMS (ESI) *m*/*z* (M + H)<sup>+</sup> calculated for (C20H32NO7) <sup>+</sup> 398.2179, found 398.2178.

#### 3.1.22. (3*S*,4*S*)-7-(aminomethyl)-5,8-dihydroxy-4-methoxy-3-pentylisochroman-1-one (**14**)

To a solution of diMOM amine derivative **14a** (4.4 mg, 11.1 μmol) in MeOH (0.83 mL) was added 6 M aqueous HCl (0.28 mL) at 0 ◦C. After stirring for 5 h at room temperature, the reaction was quenched by adding saturated aqueous NaHCO3 at 0 ◦C. The mixture was extracted with the mixture of MeOH and CH2Cl2 (MeOH:CH2Cl2 = 1:4) (×4) and the combined organic layers were dried over Na2SO4, filtered and concentrated under reduced pressure. The residue was purified with PTLC (MeOH:CHCl3 saturated with NH3 = 1:9) to give amiomethyl derivative **14** (1.1 mg, 32%) as brown solid. m.p. 78–80 ◦C; 1H-NMR (400 MHz, CDCl3) δ 6.98 (1H, s), 4.59 (1H, d, *J* = 1.8 Hz), 4.35 (1H, ddd, *J* = 1.8, 6.0, 8.0 Hz), 3.97 (1H, d, *J* = 13.3 Hz), 3.88 (1H, d, *J* = 13.3 Hz), 3.19 (3H, s), 1.98 (1H, m), 1.83 (1H, m), 1.56 (1H, m), 1.43 (1H, m), 1.40–1.25 (4H, overlapped), 0.90 (3H, t, *J* = 7.0 Hz) ; 13C-NMR (125 MHz, CDCl3) δ 169.9, 154.2, 146.2, 130.0, 125.8, 122.9, 108.1, 82.8, 68.5, 56.9, 42.3, 31.9, 30.6, 25.1, 22.8, 14,3.; IR (KBr) 2956, 2921, 2857, 1676, 1441, 1171 cm<sup>−</sup>1; HRMS (ESI) *m*/*z* (M + Na)<sup>+</sup> calculated for (C16H23NO5Na)<sup>+</sup> 332.1474, found 332.1474.
