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.
| Original language | English |
|---|---|
| Pages (from-to) | 207-213 |
| Number of pages | 7 |
| Journal | Journal of Organic Chemistry |
| Volume | 70 |
| Issue number | 1 |
| Early online date | 2 Dec 2004 |
| DOIs | |
| Publication status | Published - 7 Jan 2005 |
| Externally published | Yes |
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Cite this
Goodenough, K. M., Moran, W. J., Raubo, P., & Harrity, J. P. A. (2005). Development of a Flexible Approach to Nuphar Alkaloids via Two Enantiospecific Piperidine-Forming Reactions. Journal of Organic Chemistry, 70(1), 207-213. https://doi.org/10.1021/jo048455k