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

22 Citations (Scopus)

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 2007

Fingerprint

Narcissus
antineoplastic agents
Antineoplastic Agents
synthesis
narciclasine
tributyltin

ASJC Scopus subject areas

  • Plant Science
  • Chemistry (miscellaneous)
  • Drug Discovery
  • Organic Chemistry
  • Pharmacology

Cite this

Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine. / Pettit, George; Melody, Noeleen; Herald, Delbert L.; Knight, John C.; Chapuis, Jean.

In: Journal of Natural Products, Vol. 70, No. 3, 03.2007, p. 417-422.

Research output: Contribution to journalArticle

@article{6954eb8042d94afc97ce76c073aedb68,
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.",
author = "George Pettit and Noeleen Melody and Herald, {Delbert L.} and Knight, {John C.} and Jean Chapuis",
year = "2007",
month = "3",
doi = "10.1021/np068046e",
language = "English (US)",
volume = "70",
pages = "417--422",
journal = "Journal of Natural Products",
issn = "0163-3864",
publisher = "American Chemical Society",
number = "3",

}

TY - JOUR

T1 - Antineoplastic agents. 550. Synthesis of 10b(S)-epipancratistatin from (+)-narciclasine

AU - Pettit, George

AU - Melody, Noeleen

AU - Herald, Delbert L.

AU - Knight, John C.

AU - Chapuis, Jean

PY - 2007/3

Y1 - 2007/3

N2 - 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.

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.

UR - http://www.scopus.com/inward/record.url?scp=34247169948&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=34247169948&partnerID=8YFLogxK

U2 - 10.1021/np068046e

DO - 10.1021/np068046e

M3 - Article

VL - 70

SP - 417

EP - 422

JO - Journal of Natural Products

JF - Journal of Natural Products

SN - 0163-3864

IS - 3

ER -