A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine

Wesley J. Moran, Katharine M. Goodenough, Piotr Raubo, Joseph P.A. Harrity

Research output: Contribution to journalArticle

42 Citations (Scopus)

Abstract

A stereocontrolled route to Nuphar alkaloids is described that employs a formal [3 + 3] cycloaddition strategy to assemble the piperidine nucleus. The addition of Pd-TMM complexes to aziridine 10 was found to be sluggish; however, the addition of a functionalized allyl Grignard reagent followed by a Mitsunobu condensation reaction provided 11 in high yield. The employment of this route in the formal synthesis of (-)-deoxynupharidine 1 is described.

Original languageEnglish
Pages (from-to)3427-3429
Number of pages3
JournalOrganic Letters
Volume5
Issue number19
Early online date28 Aug 2003
DOIs
Publication statusPublished - 18 Sep 2003
Externally publishedYes

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