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.

LanguageEnglish
Pages3427-3429
Number of pages3
JournalOrganic Letters
Volume5
Issue number19
Early online date28 Aug 2003
DOIs
Publication statusPublished - 18 Sep 2003
Externally publishedYes

Fingerprint

Nuphar
alkaloids
Condensation reactions
Cycloaddition
Cycloaddition Reaction
Alkaloids
routes
piperidine
cycloaddition
synthesis
reagents
condensation
nuclei
deoxynupharidine
aziridine

Cite this

Moran, Wesley J. ; Goodenough, Katharine M. ; Raubo, Piotr ; Harrity, Joseph P.A. / A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine. In: Organic Letters. 2003 ; Vol. 5, No. 19. pp. 3427-3429.
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A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (-)-Deoxynupharidine. / Moran, Wesley J.; Goodenough, Katharine M.; Raubo, Piotr; Harrity, Joseph P.A.

In: Organic Letters, Vol. 5, No. 19, 18.09.2003, p. 3427-3429.

Research output: Contribution to journalArticle

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