Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue

  • Org Lett. 2004 Jun 24;6(13):2153-6. doi: 10.1021/ol049409+.
Oleg V Larionov  1 ,  Armin de Meijere
Affiliations
  • 1. Institut für Organische und Biomolekulare Chemie der Georg-August-Universität Göttingen, Tammannstrasse 2, D-37077 Goettingen, Germany.
PMID: 15200308 DOI: 10.1021/ol049409+
Abstract

[reaction: see text] Enantioselective total syntheses of belactosin A, belactosin C, and its homoanalogue have been accomplished in high overall yields (32% for belactosin A from the amino acid 10, and 35 and 36% for belactosin C and its homoanalogue, respectively). This concise approach comprises a novel sequential acylation/beta-lactonization reaction and allows a facile alteration of the substituents, thus providing a flexible route to a new family of highly active belactosin-based Proteasome inhibitors.

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