SYNTHESIS OF 9-EPI (TRANS FUSED) LACTARANE SESQUITERPENES

Oxidation of furandiol to its 8-keto-derivative, followed by enolizati on and sodium borohydride reduction gave 8-epi-9-epi-furandiol, a tran s fused lactarane sesquiterpene, in good yield. Structure of the new c ompound was substantiated by H-1 NMR spectroscopy and confirmed by X-r ay diffraction method. The almost quantitative isomerization of furand iol into its 8-epi-9-epi derivative was explained in terms of molecula r energy calculations using PCMODEL4 computer program. 8-Epi-9-epi-fur andiol served as a starting material for the preparation of a series o f trans fused lactarane sesquiterpenes