A SHORT AND FLEXIBLE ENANTIOSELECTIVE SYNTHESIS OF THE DIDEMNENONES

By simple variation of conditions for the elimination reaction, the unsaturated lactones 2 (R = CH = CH2, R' = H) or 2' (R = H, R' = CH = CH2) may be prepared from 1. The reduction of 2 affords, after the removal of the protecting groups, the mixture of epimeric lactols 3a (X = alpha-...

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Published inAngewandte Chemie International Edition Vol. 30; no. 2; pp. 191 - 192
Main Authors BAUERMEISTER, H, RIECHERS, H, SCHOMBURG, D, WASHAUSEN, P, WINTERFELDT, E
Format Journal Article
LanguageEnglish
Published WEINHEIM Wiley 01.02.1991
Subjects
Chemistry
Chemistry, Multidisciplinary
Physical Sciences
Science & Technology
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Summary:By simple variation of conditions for the elimination reaction, the unsaturated lactones 2 (R = CH = CH2, R' = H) or 2' (R = H, R' = CH = CH2) may be prepared from 1. The reduction of 2 affords, after the removal of the protecting groups, the mixture of epimeric lactols 3a (X = alpha-OH) and 3b (X = beta-OH), identical to the naturally occurring compounds, while 2' yields the corresponding "isomeric" didemnenones. R" = SitBuMe2.
ISSN:1433-7851
DOI:10.1002/anie.199101911