A SHORT SYNTHESIS OF DIASTEREOMERIC NORAMBRAKETALS

Authors
ANDREEVA IY ARYKU AN VLAD PF
Citation
Iy. Andreeva et al., A SHORT SYNTHESIS OF DIASTEREOMERIC NORAMBRAKETALS, Russian chemical bulletin, 47(6), 1998, pp. 1162-1165
Citations number
9
Categorie Soggetti
Chemistry
Journal title
Russian chemical bulletin → ACNP
ISSN journal
10665285
Volume
47
Issue
6
Year of publication
1998
Pages
1162 - 1165
Database
ISI
SICI code
1066-5285(1998)47:6<1162:ASSODN>2.0.ZU;2-J
Abstract
A short synthesis of diastereomeric norambraketals was accomplished st arting from norambreinolide. The reaction of norambreinolide with meth yllithium followed by dehydration of the obtained 8 alpha-hydroxy-14,1 5,16-trinorlabdan-12-one gave 14,15,16-trinorlabd-8(17)-en-12-one. Oxi dation of the latter with OsO4 or peracids with subsequent isomerizati on of the formed epoxy ketone leads, respectively, to (12R)-8 alpha,12 :12,17- and (12S)-8 beta,12:12,17-diepoxy-14,15,16- trinorlabdans. Onl y the former is fragrant and possesses ambergris odor.