2. Academic Validation
  3. Antineoplastic agents. 550. Synthesis of 10b(s)-epipancratistatin from (+)-narciclasine

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

  • J Nat Prod. 2007 Mar;70(3):417-22. doi: 10.1021/np068046e.
George R Pettit 1,  Noeleen Melody,  Delbert L Herald,  John C Knight,  Jean-Charles Chapuis
Affiliations

Affiliation

  • 1 Cancer Research Institute and Department of Chemistry and Biochemistry, Arizona State University, P.O. Box 872404, Tempe, AZ 85287-2404, USA. bpettit@asu.edu
PMID: 17346078 DOI: 10.1021/np068046e
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.

Figures