Chemo-enzymatic synthesis of (-)-epipentenomycin I

Authors

Tawesin Klomklao, Chiang Mai University
Stephen G. Pyne, University of WollongongFollow
Apiwat Baramee, Chiang Mai University
Brian W. Skelton, University of Western Australia
Allan H. White, University of Western Australia

RIS ID

9897

Publication Details

Pyne, S. G., Klomklao, T., Baramee, A., Skelton, B. W. & White, A. H. (2003). Chemo-enzymatic synthesis of (-)-epipentenomycin I. Tetrahedron-Asymmetry, 14 3885-3889.

Abstract

A chemo-enzymatic synthesis of (−)-epipentenomycin I is reported using a lipase-catalysed kinetic resolution of the racemic pentacyclic alcohol 8. Flash vacuum pyroloysis of (−)-8 so obtained gave (−)-(4R)-4-hydroxy-5-methylene-2-cyclopentenone. Epoxidation of this compound with dimethyldioxirane followed by hydrolytic ring-opening of the resulting epoxide gave (−)-epipentenomycin I.