Sulcatol formation

Comparable results were also reported by another group [65]. Controlled conversion of 6-methyl-5-hepten-2-one by Botrytis cinerea resulted in the formation of (5)-(+)-6-methyl-5-hepten-2-ol (sulcatol) of 90% ee. In addition, (2R,5R), (25,55)-, (2R,5S) and (25,5/ )-pityol and the four enantiomers of 3-hydroxy-2,2,6-trimethyltetrahydropyran were found as biotransformation products of 6-methyl-5-hepten-2-one. 

Enantiomerically pure propeneoxide can be obtained in three steps from lactic acid. Its reaction with prenyl cuprate directly yields sulcatol [9, 10]. Even with such a convincing route at hand, one should not fail to evaluate routes via a racemate. A classical resolution via the formation of a hemiphthalate and crystallization of its brucine salt appears circumstantial. Yet kinetic resolution using enzymes, e.g.. Upases, appears more attractive (Scheme 10.7) [11]. 

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