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

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

doi:10.1021/np068046e

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 journal › Article

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 language	English (US)
Pages (from-to)	417-422
Number of pages	6
Journal	Journal of Natural Products
Volume	70
Issue number	3
DOIs	https://doi.org/10.1021/np068046e
State	Published - Mar 1 2007

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ASJC Scopus subject areas

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

Cite this

Pettit, G., Melody, N., Herald, D. L., Knight, J. C., & Chapuis, J. (2007). Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine. Journal of Natural Products, 70(3), 417-422. https://doi.org/10.1021/np068046e

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10.1021/np068046e