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
- 1 January 1992
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1992 (04) , 272-274
- https://doi.org/10.1055/s-1992-21336
Abstract
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.Keywords
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