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(±)-α-Cyclogeraniol and (±)-drim-7-en-11-ol acetates obtained via the FSO
3H-induced cyclisation of geraniol and (
E)-farnesol and subsequent acetylation were hydrolysed in the presence of hog pancreas lipase (PPL) to afford (
R)-(+)-α-cyclogeraniol (ee ∼30% at the optimal conversion
C = 20±2%) and (5
R,9R,10R)-(+)-drim-7-en-11-ol (
ee 78.5% at
C = 30%), respectively; (±)-15-acetoxyisoagath-12-ene, obtained similarly from all-
E-geranylgeraniol, is resistant to PPL-mediated hydrolysis, but is hydrolysed in the presence of lipase from
Candida cylindracea to afford (10S,14
R)-(−)-isoagath-12-en-15-ol of 69–80%
ee in ∼3% yield.