SYNTHESIS OF 9-EPI (TRANS FUSED) LACTARANE SESQUITERPENES

Citation
Wm. Daniewski et al., SYNTHESIS OF 9-EPI (TRANS FUSED) LACTARANE SESQUITERPENES, Polish Journal of Chemistry, 68(2), 1994, pp. 287-295
Citations number
11
Categorie Soggetti
Chemistry
Journal title
ISSN journal
01375083
Volume
68
Issue
2
Year of publication
1994
Pages
287 - 295
Database
ISI
SICI code
0137-5083(1994)68:2<287:SO9(FL>2.0.ZU;2-Z
Abstract
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