Antineoplastic agents. 571. total synthesis of bacillistatin 2

George Pettit, Shougang Hu, John C. Knight, Jean Chapuis

Research output: Contribution to journalArticle

14 Scopus citations

Abstract

The first total synthesis of bacillistain 2 (2) has been achieved in 24 steps and 22.9% overall yield, providing a quite efficient route with maximal convergence. Notable features of this approach include two successful applications of the Mitsunobu reaction during respective assemblies of key intermediates 22 and 27, successful employment of 2-methyl- 6-nitrobenzoic anhydride (MNBA) in the formation by lactonization of a macrocyclic (36-membered) ring, and very flexible access to structural modifications of the bacillistatin-type cyclodepsipeptides.

Original languageEnglish (US)
Pages (from-to)372-379
Number of pages8
JournalJournal of Natural Products
Volume72
Issue number3
DOIs
StatePublished - Mar 27 2009

ASJC Scopus subject areas

  • Analytical Chemistry
  • Molecular Medicine
  • Pharmacology
  • Pharmaceutical Science
  • Drug Discovery
  • Complementary and alternative medicine
  • Organic Chemistry

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