Antineoplastic agents. 561. Total synthesis of respirantin

George Pettit, Thomas H. Smith, Song Feng, John C. Knight, Rui Tan, Robin Pettit, Peter A. Hinrichs

Research output: Contribution to journalArticlepeer-review

28 Scopus citations

Abstract

Total synthesis of the 18-membered ring cyclodepsipeptide believed to be respirantin (1b) has been achieved. The key step in the synthesis is an intramolecular transesterification of the β-ketoester alcohol 6 to afford the protected macrocycle 5. The synthetic product was shown to be identical to a natural product presumed to be respirantin (1b), and the absolute stereochemistry of six of the seven asymmetric centers of cyclodepsipeptide 1b was unequivocally established. Respirantin (1b) was found to be a remarkable inhibitor of cancer cell growth and related to the antimycin family of antibiotics.

Original languageEnglish (US)
Pages (from-to)1073-1083
Number of pages11
JournalJournal of Natural Products
Volume70
Issue number7
DOIs
StatePublished - Jul 2007

ASJC Scopus subject areas

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

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