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 › peer-review

22 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 2007

ASJC Scopus subject areas

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

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

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.",

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AU - Pettit, George

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AU - Knight, John C.

AU - Chapuis, Jean

PY - 2007/3

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AB - 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.

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