3.1.11. *1,7-bis(4-Hydroxy-3-methoxyphenyl)-4,4-dimethylheptane-3,5-dione* (**19**) *and 5-hydroxy-1,7-bis(4 hydroxy-3-methoxyphenyl)-4,4-dimethylheptan-3-one* (**20**)

To a stirred solution of compound **2m** (0.885 g, 2.23 mmol) in MeOH (10 mL) was added Pd/C (45 mg, 10% *w*/*w*) in one portion. The resulting mixture was hydrogenated under 1 atmosphere of H2 at room temperature. After 2 h, the mixture was filtered by celite and concentrated to give the crude product, which was purified by flash chromatography on silica gel with EtOAc/*n*-hexane/ (1:2) to afford compound **19** (465 mg, 52% yield) as a colorless oil and compound **20** (206 mg, 23% yield) as a colorless oil.

Compound **19**: 1H-NMR (CDCl3) δ 6.83 (d, *J* = 8.0 Hz, 2H), 6.65 (d, *J* = 2.0 Hz, 2H), 6.63–6.61 (m, 2H), 5.51 (s, 2H), 3.87 (s, 6H), 2.76 (t, *J* = 7.0 Hz, 4H), 2.58 (t, *J* = 7.0 Hz, 4H), 1.29 (s, 6H); 13C-NMR (CDCl3) δ 208.9, 146.4, 143.9, 132.7, 120.9, 114.3, 114.9, 111.7, 62.4, 55.9, 40.5, 29.4, 21.0; HRMS [ESI]<sup>+</sup> calculated for C23H28NaO6: 423.1784 [M + Na]+; found: 423.1780.

Compound **20**: 1H-NMR (CDCl3) δ 6.86–6.83 (m, 2H), 6.72–6.66 (m, 4H), 5.62–5.61 (br s, 2H), 3.89 (s, 3H), 3.87 (s, 3H), 3.71–3.69 (m, 1H), 2.90–2.71 (m, 5H), 2.61–2.51 (m, 2H), 1.71–1.55 (m, 2H), 1.13 (s, 3H), 1.08 (s, 3H); 13C-NMR (CDCl3) δ 216.5, 146.4, 143.9, 143.7, 133.9, 133.1, 120.9, 120.8, 114.4, 114.3, 111.2, 111.1, 55.9, 51.7, 40.3, 33.7, 32.6, 29.4, 21.7, 19.3; HRMS [ESI]<sup>+</sup> calculated for C23H30NaO6: 425.4768 [M + Na]+; found: 425.4760.
