Download PDF
Synlett 1992; 1992(4): 272-274
DOI: 10.1055/s-1992-21336
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.

Efficient Preparation of Useful 1,2-Substituted Electron-Deficient Dienes from Sulpholenes and Their Use in Intramolecular Diels-Alder Reactions: A General Approach to Alkaloids

John Leonard* , Stephen P. Fearnley, Deirdre M. B. Hickey
  • *Department of Chemistry, University of Salford, Salford M5 4WT, England
Further Information

Publication History

Publication Date:
08 March 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

A short, efficient sequence is described for the conversion of 3-methoxycarbonyl-3-sulpholene [3-methoxycarbonyl-2,5-dihydrothiophene 1,1-dioxide (3)] into 2,3-disubstituted diene precursors bearing an ester or amide at the 3-position. The trans-1,2,3,4,4a,7,8,8a-octahydroisoquinolines 12 and 13 are prepared selectively from the sulpholenes via intramolecular exo Diels-Alder reactions.