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Synlett 1992; 1992(4): 272-274
DOI: 10.1055/s-1992-21336
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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
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Publication Date:
08 March 2002 (online)

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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.

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