Simple approach to optically active drimane sesquiterpenes based on enzymatic resolution

Article abstract of DOI:10.1248/cpb.45.824

When the β-acyloxy esters (±)-10 and (±)-II were exposed to the lipase OF-360 from Candida rugosa or immobilized lipase OF-360 in a water- saturated organic solvent, the hydrolyzed product (8aS)-6 was obtained in high chemical (40%) and optical (>99%ee) yields. The absolute structure of (8aS)-6 was confirmed by the fact that (8aS)-6 was converted into an authentic sample γ-keto nitrile (8aS)-17. Treatment of the diol (±)-12 with isopropenyl acetate in the presence of the lipase Godo E-4 from Pseudomonas sp. provided the unchanged (8aR)-12 (89% ee) in 42% yield.

Full text of DOI:10.1248/cpb.45.824

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