Synlett 1994; 1994(5): 335-336
DOI: 10.1055/s-1994-22844
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.

The First Synthesis of (±)-Taxodone

Anthony J. Sánchez* , Joseph P. Konopelski
  • *Department of Chemistry and Biochemistry, University of California, Santa Cruz, California 95064, USA
Further Information

Publication History

Publication Date:
22 March 2002 (online)

The total synthesis of (±)-taxodone (1) is described. The C-ring is formed by the cycloaddition of methyl acrylate with siloxyfuran 5 derived from isodrimenin (4). The C13 isopropyl group was introduced via a sulfur ylide rearrangement followed by reductive cleavage. Compound 1 was synthesized in 61% yield from diacetate 18 by deprotection and intramolecular oxirane opening with potassium t-butoxide and water in THF