PDF herunterladen
Synlett 1995; 1995(6): 607-608
DOI: 10.1055/s-1995-5018
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

Synthesis of ent-Cheilanthenediol, the Enantiomer of a Natural Tricyclopentaprenediol

Thierry Jenn, Denis Heissler*
  • *Institut de Chimie, URA CNRS 31, Université Louis Pasteur, BP 296, 67008 Strasbourg, France
Weitere Informationen

Publikationsverlauf

Publikationsdatum:
31. Dezember 2000 (online)

  als PDF herunterladen  Lizenzen und Reprints Alle Artikel dieser Rubrik

This synthesis of the sesterterpene ent-cheilanthenediol is based on the addition of the isocopal-12-en-15-yl radical to monoprotected methyl 3,4-dihydroxy-2-methylenebutanoate which has been prepared from protected hydroxyacetaldehyde by a Baylis-Hillman reaction. The equatorial tertiary hydroxyl group at C-13 has been obtained by opening an epoxide with lithium diisobutyl-n-butylaluminium hydride.

Baylis-Hillman reaction - radical addition - cis double bond formation - epoxide opening - lithium diisobutyl-n-butyl-aluminium hydride