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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
Metadata only available from this repository.Official URL: http://dx.doi.org/10.1021/ol035156t
DOI: 10.1021/ol035156t
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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