PREPARATION OF POLYOXYGENATED ENT-13-EPI-MANOYL OXIDES BY CHEMICAL MICROBIOLOGICAL SEMISYNTHESES

The biotransformation of ent-3 beta-hydroxy-13-epi-manoyl oxide with F usarium moniliforme gave ent-7 beta, 11 alpha-dihydroxy, ent-7 beta, 1 2 alpha-dihydroxy derivatives and the corresponding products oxidized at C-3. The biotransformation of ent-3-oxo-13-epi-manoyl oxide with Fu sarium moniliforme gave ent-1 beta-hydroxy and Delta(1)-derivatives. T he incubation of ent-3, 12-dioxo-13-epi-manoyl oxide with Fusarium mon iliforme gave ent-11 alpha-hydroxy, ent-1 beta-hydroxy and ent-7 beta, 11 alpha-dihydroxy derivatives, and with Cunninghamella elegans gave the 14, 15-dihydroxy derivative. The biotransformation of ent-3 beta,1 2 beta-dihydroxy-13-epi-manoyl oxide with Rhizopus nigricans gave the ent-7 alpha-hydroxy derivative.