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

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

doi:10.1021/ol035156t

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 journal › Article › peer-review

47 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 language	English
Pages (from-to)	3427-3429
Number of pages	3
Journal	Organic Letters
Volume	5
Issue number	19
Early online date	28 Aug 2003
DOIs	https://doi.org/10.1021/ol035156t
Publication status	Published - 18 Sept 2003
Externally published	Yes

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10.1021/ol035156t

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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.",

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AU - Goodenough, Katharine M.

AU - Raubo, Piotr

AU - Harrity, Joseph P.A.

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N2 - 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.

AB - 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.

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

Abstract

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