Harkiss, A. H. and Sutherland, A. (2018) Access to 2,6-disubstituted 4-oxopiperidines using a 6-endo-trig cyclization: stereoselective synthesis of spruce alkaloid and (+)-241D. Journal of Organic Chemistry, 83(1), pp. 535-542. (doi: 10.1021/acs.joc.7b02799) (PMID:29218988)
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Abstract
A synthetic route to cis-2-methyl-4-oxo-6-alkylpiperidines has been developed using a 6-endo-trig cyclization of E-enones. The base-mediated intramolecular cyclization was found to be general for both alkyl and aryl substituted enones, providing the corresponding 4-oxopiperidines in high yields (80–89%). Stereoselective reduction of the 2,6-cis-disubstituted 4-oxopiperidines then gave the 2,4,6-cis,cis-trisubstituted 4-hydroxypiperidines in high diastereoselectivity. The general nature of this approach was demonstrated with the synthesis of the natural products, spruce alkaloid and (+)-241D.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Sutherland, Professor Andrew and Harkiss, Dr Alexander |
| Authors: | Harkiss, A. H., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Journal of Organic Chemistry |
| Publisher: | American Chemical Society |
| ISSN: | 0022-3263 |
| ISSN (Online): | 1520-6904 |
| Published Online: | 08 December 2017 |
| Copyright Holders: | Copyright © 2017 American Chemical Society |
| First Published: | First published in Journal of Organic Chemistry 83(1):535-542 |
| Publisher Policy: | Reproduced in accordance with the publisher copyright policy |
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