Reaction Steps
Osmium tetraoxide (80 mg, 0.3 mmol) was added to a solution of [S-(3R*,5R*,6R*)-2-ethyl-3,5-dimethyl-1-octen-6-ol (15a) (0.552 g, 3 mmol) in 36 mL of 1,4-dioxane and 12 mL of water at 20°-25° C. After 15 min, finely powdered sodium periodate (10.0 g, 46.8 mmol) was added in several portions over a period of 1 h, in accord with the literature procedure [Pappo, R. et al., J. Org. Chem., 1956, 21:478-479]. The mixture was stirred for 16 h, then extracted with ether (2∞50 mL). The ether solution was washed with sodium sulfite solution, dried over anhydrous magnesium sulfate (0.5 g), filtered, and concentrated at 50 torr to yield a residue of serricornin (1 and 2) (0.507 g, 91%). The NMR data are consistent with those previously reported [Mori, K. and Watanabe, H., Tetrahedron, 1985, 41:3423-3428]:300 MHz 1H-NMR (C6 D6) (literature data in parentheses) δ0.8-2.4 (m, 23), 3.2 (lit 3.17) (m, 0.75, CH--O of 2), 3.75 (lit 3.82) (ddd, 0.25, CH--O of 1); 75 MHz 13C-NMR (C6D6), assigned to 1:δ8.0, 10.7, 14.0, 16.5, 27.0, 33.9, 36.1, 36.8, 43.6, 76.4, 213.4 (8.0, 10.8, 13.7, 16.4, 27.5, 33.9, 35.8, 36.8, 43.8, 76.4, 213.6); assigned to 2:7.4, 10.7, 11.7, 16.8, 26.2, 30.2, 31.3, 33.1, 36.1, 72.6, 98.5 (7.4, 10.7, 11.7, 16.7, 26.2, 30.2, 31.3, 33.1, 36.2, 72.7, 98.6), HRMS: calcd for C11 H20O [(M-18)+] 168.1514; found, 168.1506.
