Journal of Synthetic Organic Chemistry, Japan
Online ISSN : 1883-6526
Print ISSN : 0037-9980
ISSN-L : 0037-9980
Biochemical Resolution of (±) -Terpenic alcohols by Microbial Hydrolysis of Corresponding Acetates.
Takayuki ORITANIKyohei YAMASHITA
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1983 Volume 41 Issue 11 Pages 1054-1063

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Abstract
By selected microorganisms (±) - cyclic terpenealcohols (menthols, carvomenthols, isopulegols, carveols and borneols) were resolved via asymmetric hydrolysis of the corresponding acetates and chloroacetates at the high concentrations (110 %) of racemic substrates. Generally, the acetates of (1 R) -2, 5- disubstituted 1- cyclohexanols were hydrolyzed faster than those of their enantiomeric (1 S) - alcohols. On the contrary, the acetates of (1 S) -sec- acyclic alcohols faster than those of their enantiomeric (1 R) - alcohols. Optical purities of separated alcohols were changed by microorganisms used and hydrolysis ratios. This microbial resolution was used effectively for syntheses of chiral building blocks for optically active carotenoids and cycloheximide antibiotic.
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© The Society of Syhthetic Organic Chemistry, Japan
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