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

Moran, Wesley J., Goodenough, Katharine M., Raubo, Piotr and Harrity, Joseph P. A. (2003) A Concise Asymmetric Route to Nuphar Alkaloids. A Formal Synthesis of (−)-Deoxynupharidine. Organic Letters, 5 (19). pp. 3427-3429. ISSN 15237060

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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.

Item Type: Article
Subjects: Q Science > Q Science (General)
Q Science > QD Chemistry
Schools: School of Applied Sciences
School of Applied Sciences > Biomolecular Sciences Research Centre
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Depositing User: Graham Stone
Date Deposited: 24 Apr 2009 11:39
Last Modified: 02 Jun 2009 13:40
URI: http://eprints.hud.ac.uk/id/eprint/4038

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