Download PDF
Synlett 2000; 2000(4): 541-543
DOI: 10.1055/s-2000-6575
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.

An Efficient Total Synthesis of Isodrimeninol from Zamoranic Acid

Isidro S. Marcos* , Rosalina F. Moro, Santiago Carballares M., Julio G. Urones
  • *Dept. de Química Orgánica, Universidad de Salamanca, Plaza de los Caídos 1-5, 37008 Salamanca, Spain; Fax +34 9 23 29 45 74; E-mail: rfm@gugu.usal.es
Further Information

Publication History

Publication Date:
31 December 2000 (online)

  PDF Download  Permissions and Reprints All articles of this category

An efficient total synthesis of isodrimeninol (1) has been achieved from zamoranic acid (3) employing a regioselective Lewis acid mediated elimination-isomerisation as the key step. Following oxidative cleavage of the resulting conjugated diene to the methyl ketone, standard manipulations allowed the synthesis of allylic alcohols 10 which, after a highly diastereoselective epoxidation and subsequent lactonisation, allowed the synthesis of the natural product in 11 steps and 56% overall yield.

regioselective acid-catalysed elimination - γ-lactones - δ-lactones - bioactive drimanes - diastereoselective epoxidation

      >