Document Report Card

ID: ALA1142985

Journal: J Nat Prod

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

Authors: Pettit GR, Melody N, Herald DL, Knight JC, Chapuis JC.

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.

CiteXplore: 17346078

DOI: 10.1021/np068046e