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