Enzymatic resolution of (±)-γ-cyclohomogeraniol and conversion of its (S)-Isomer to (S)-γ-coronal, the ambergris odorant1 In memory of Professor Sir Derek H. R. Barton with full respect and thanks for his unforgettable encouragement to K. M.12 Preparative Bioorganic Chemistry, Part 19. For Part 18, see ref .2
Enzymatic acetylation of (±)-γ-cyclohomogeraniol[2-(2′,2′-dimethyl-6′-methylenecyclohexyl)ethanol] with vinyl acetate in the presence of lipase AK yielded the acetate of its (
R)-isomer, leaving its (
S)-isomer intact. The (
S)-isomer was chemically converted to (
S)-γ-coronal[2-methylene-4-(2′,2′-dimethyl-6′-methylenecyclohexyl)butanal], the ambergris odorant.