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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 and Harrity, Joseph P. A. (2005) Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions. The Journal of Organic Chemistry, 70 (1). pp. 207-213. ISSN 00223263

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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.

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 11:29
Last Modified: 09 Sep 2010 09:42
URI: http://eprints.hud.ac.uk/id/eprint/4036

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