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MODEL STUDIES RELATED TO THE TOTAL SYNTHESIS OF THE FUMITREMORGINS - THE PICTET-SPENGLER CYCLIZATION AND THE FORMATION AND INTRAMOLECULAR ACYLATION OF A 1,2-DIHYDRO-BETA-CARBOLINE DERIVATIVE

Publisher
PERGAMON-ELSEVIER SCIENCE LTD
Publication Date
Keywords
  • Qd Chemistry

Abstract

The preparations of the tetrahydro-beta-carbolines 8, 9b, and 9d are described. The Pictet-Spengler reaction of L-tryptophyl-L-proline methyl ester with 3-methylbutanal gave the tetrahydro-beta-carbolines 20 and 21; subsequent acid-catalysed cyclisation afforded the fumitremorgin analogues 22 and 23. The 2-(p-toluenesulphonyl)tetrahydro-beta-carboline 27a furnished the unsaturated pentacycle 28a upon treatment with alkali.

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