STUDIES ON THE SYNTHESIS OF SCOPARIC ACID-A AND RELATED LABDANE DITERPENOIDS - SYNTHESIS OF (E)-6-BETA-HYDROXLABDA-8-(17),13-DIEN-15-OIC ACID

A general strategy fbr a successful approach to labdanes of the type 3-5 is described. This methodology, which makes use of the known Eschenmoser fragmentation of 9, 1,3-oxidative rearrangement of allylic tertiary alcohol 14, and photochemical double bond isomerization of allylic acetate 17 as key s...

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Bibliographic Details
Published inJournal of natural products (Washington, D.C.) Vol. 56; no. 12; pp. 2133 - 2141
Main Authors ABAD, A, ARNO, M, AGULLO, C, CUNAT, AC, MESEGUER, B, ZARAGOZA, RJ
Format Journal Article
LanguageEnglish
Published WASHINGTON Amer Chemical Soc 01.12.1993
Subjects
Chemistry, Medicinal
Life Sciences & Biomedicine
Pharmacology & Pharmacy
Plant Sciences
Science & Technology
COMPLEX
DULCIS
REACTIVITY
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Summary:A general strategy fbr a successful approach to labdanes of the type 3-5 is described. This methodology, which makes use of the known Eschenmoser fragmentation of 9, 1,3-oxidative rearrangement of allylic tertiary alcohol 14, and photochemical double bond isomerization of allylic acetate 17 as key synthetic steps, is used to prepare optically pure labdane 5 from readily available (+)-podocarpenone 8.
ISSN:0163-3864
DOI:10.1021/np50102a016