Chemo-enzymatic synthesis of (-)-epipentenomycin I

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.