Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions

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

Research output: Contribution to journalArticle

67 Citations (Scopus)

Abstract

In this paper we describe the stereoselective synthesis of functionalized lactam 7 via two enantiospecific piperidine-forming techniques and its employment in a general synthetic approach to Nuphar alkaloids. Specifically, the formation of piperidine 18 by formal [3 + 3] cycloaddition and stepwise annelation processes is described; the latter technique was found to be significantly more efficient than the Pd-catalyzed TMM addition process. Finally, exploitation of the exocyclic alkene installed in the piperidine-forming reaction in the transformation of 18 to (-)-deoxynupharidine ((-)-2), (-)-castoramine ((-)-3), and (-)-nupharolutine ((-)-4) via intermediate lactam 7 is delineated.

LanguageEnglish
Pages207-213
Number of pages7
JournalJournal of Organic Chemistry
Volume70
Issue number1
Early online date2 Dec 2004
DOIs
Publication statusPublished - 7 Jan 2005
Externally publishedYes

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Alkaloids
Lactams
Cycloaddition
Alkenes
piperidine

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Goodenough, Katharine M. ; Moran, Wesley J. ; Raubo, Piotr ; Harrity, Joseph P.A. / Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions. In: Journal of Organic Chemistry. 2005 ; Vol. 70, No. 1. pp. 207-213.
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Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions. / Goodenough, Katharine M.; Moran, Wesley J.; Raubo, Piotr; Harrity, Joseph P.A.

In: Journal of Organic Chemistry, Vol. 70, No. 1, 07.01.2005, p. 207-213.

Research output: Contribution to journalArticle

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