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Enzyme‐Mediated Preparation of Enantiomerically Pure p ‐Menthan‐ 3,9‐diols and Their Use for the Synthesis of Natural p ‐Menthane Lactones and Ethers
Author(s) -
Serra Stefano,
Fuganti Claudio
Publication year - 2002
Publication title -
helvetica chimica acta
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.74
H-Index - 82
eISSN - 1522-2675
pISSN - 0018-019X
DOI - 10.1002/1522-2675(200208)85:8<2489::aid-hlca2489>3.0.co;2-9
Subject(s) - chemistry , kinetic resolution , enantiomer , lipase , organic chemistry , lactone , odor , diol , acetylation , enzyme , stereochemistry , enantioselective synthesis , catalysis , biochemistry , gene
The diastereoselective preparation of the p ‐menthane‐3,9‐diols (±)‐ 12 , (±)‐ 13a , (±)‐ 13b , and (±)‐ 18 and the study of their enzymic resolution is described ( Scheme 1 ). The corresponding enantiomer‐enriched diols obtained by means of the lipase‐mediated kinetic acetylation of the racemic diols are suitable synthetic precursors of many relevant p ‐menthane monoterpenes. Their usefulness is shown in the preparation of different natural products of this class that are interesting for industrial purposes because of their odor qualities, i.e. , of the enantiomeric form of 3‐hydroxy‐ p ‐menthan‐9‐oic acid lactone 1 , of mintlactone 2 , of the 3,9‐epoxy‐ p ‐menth‐1,8(10)‐diene 10 , and of the pheromone vesperal 11 ( Schemes 2 and 3 ).