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
Metadata only available from this repository.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 |
Related URLs: | |
Depositing User: | Graham Stone |
Date Deposited: | 24 Apr 2009 10:29 |
Last Modified: | 28 Aug 2021 10:46 |
URI: | http://eprints.hud.ac.uk/id/eprint/4036 |
Downloads
Downloads per month over past year
Repository Staff Only: item control page
![]() |
View Item |