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