Water → (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene

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To a solution of (1R,2R,4aS,8aS)-1-{[(3,5-dimethoxyphenyl)sulfanyl]-methyl}-2,5,5,8a-tetramethyl-decahydronaphthalen-2-ol (21) (1.0 g, 2.55 mmol) in CH2Cl2 (50 mL) was added dropwise SnCl4 (1 M in CH2Cl2, 10.2 mL, 10.19 mmol) at −78° C. over 5 min. After complete addition, the reaction mixture was allowed to warm to 0° C. for 1 h, then room temperature for 2 h. Water (20 mL) was added at room temperature followed by CH2Cl2 (50 mL). The organic layer was separated, dried (Na2SO4), and concentrated. Trituration with MeOH gave (1R,10R,11S,16S)-3,5-dimethoxy-1,11,15,15-tetramethyl-8-thiatetracyclo[8.8.0.02,7.011,16]octadeca-2,4,6-triene (Compound No. 22) (0.77 g, 81%) as a white solid. 1H NMR (CDCl3): δ 6.22 (d, 1H), 6.18 (d, 1H), 3.78 (s, 3H), 3.78 (s, 3H), 3.25 (m, 1H), 2.90 (m, 1H), 2.78 (m, 1H), 1.84-1.38 (m, 7H), 1.37 (s, 3H), 1.36-1.00 (m, 3H), 0.95 (s, 3H), 0.90 (m, 1H), 0.85 (s, 3H), 0.85 (s, 3H). MS m/z 375 (C23H34O2S+H+).

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