Antineoplastic agents. 450. Synthesis of (+)-pancratistatin from (+)-narciclasine as relay

George Pettit, Noeleen Melody, D. L. Herald

Research output: Contribution to journalArticle

103 Scopus citations

Abstract

(+)-Narciclasine (2) available in quantity from certain Amaryllidaceae species or by total synthesis was employed as a precursor for a 10-step synthetic conversion (3.6% overall yield) to natural (+)-pancratistatin (1a). The key procedures involved epoxidation of natural (+)-narciclasine (2) to epoxide 6, reduction to diol 8, and formation of cyclic sulfate 12 and its ring opening with cesium benzoate followed by saponification of the benzoate to afford (+)-pancratistatin (1a).

Original languageEnglish (US)
Pages (from-to)2583-2587
Number of pages5
JournalJournal of Organic Chemistry
Volume66
Issue number8
DOIs
StatePublished - Apr 20 2001

ASJC Scopus subject areas

  • Organic Chemistry

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