111319-95-0Relevant articles and documents
Chemoenzymatic preparation of the p-menth-1,5-dien-9-ol stereoisomers and their use in the enantiospecific synthesis of natural p-menthane monoterpenes
Serra, Stefano,Nobile, Igor
experimental part, p. 1455 - 1463 (2011/11/12)
A study on the preparation and synthetic exploitation of the isomeric forms of p-menth-1,5-dien-9-ol is reported. The latter alcohols were prepared in high enantiomeric purity from the easily available enantiomers of carvone. Thus, a chemoenzymatic procedure based on lipase-mediated acetylation, allowed the separation of their diastereoisomeric forms. Moreover, the purity of the chiral building blocks obtained was improved by fractional crystallisation of their 3,5-dinitrobenzoyl derivatives. A number of synthetic applications have also been described. The stereospecific cyclisation of the isomerically pure dienic alcohols gave the isomeric forms of the terpenes dill and epi-dill ether, which were hydrogenated diastereoselectively to the corresponding (1R)- or (1S)-derivatives depending on the catalyst used. The oxidation of the latter ethers turned out to be stereoselective, affording either the corresponding p-menthan-9-oic lactone or the keto-acid derivatives depending on the starting isomer used.
