Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine

George Pettit, Noeleen Melody, Delbert L. Herald, John C. Knight, Jean Chapuis

Research output: Contribution to journalArticle

21 Scopus citations

Abstract

By means of a five-step reaction sequence, narciclasine (2a), isolated from Narcissus sp., was converted to 10b(S)-epipancratistatin (3a) in 5.7% overall yield. The key step entailed a radical-initiated 10b,1 C-O cleavage employing tributyltin hydride to yield a B/C cis ring juncture (3b). Biological evaluation of 10b(S)-epipancratistatin (3a) provided evidence that antineoplastic activity was reduced by a factor of 10 when the B/C trans juncture was replaced with a B/C cis ring juncture.

Original languageEnglish (US)
Pages (from-to)417-422
Number of pages6
JournalJournal of Natural Products
Volume70
Issue number3
DOIs
StatePublished - Mar 1 2007

    Fingerprint

ASJC Scopus subject areas

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

Cite this