Bell, J. D., Harkiss, A. H., Wellaway, C. R. and Sutherland, A. (2018) Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation. Organic and Biomolecular Chemistry, 16(35), pp. 6410-6422. (doi: 10.1039/C8OB01363B) (PMID:30011344)
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Abstract
An acid-mediated 6-endo-trig cyclisation of amine-substituted enones has been developed for the stereoselective synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines. Performed under conditions that prevent removal of the Boc-protecting group or acetal formation, the key cyclisation was found to generate cleanly the 4-oxopiperidine products in high overall yields from a wide range of alkyl substituted enones. The synthetic utility of the trans-6-alkyl-2-methyl-4-oxopiperidines formed from this process was demonstrated with the total synthesis of the quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (–)-solenopsin A.
| Item Type: | Articles |
|---|---|
| Status: | Published |
| Refereed: | Yes |
| Glasgow Author(s) Enlighten ID: | Harkiss, Dr Alexander and Bell, Mr Jonathan and Sutherland, Professor Andrew |
| Authors: | Bell, J. D., Harkiss, A. H., Wellaway, C. R., and Sutherland, A. |
| College/School: | College of Science and Engineering > School of Chemistry |
| Journal Name: | Organic and Biomolecular Chemistry |
| Publisher: | Royal Society of Chemistry |
| ISSN: | 1477-0520 |
| ISSN (Online): | 1477-0539 |
| Published Online: | 11 July 2018 |
| Copyright Holders: | Copyright © 2018 The Authors |
| First Published: | First published in Organic and Biomolecular Chemistry 16(35):6410-6422 |
| Publisher Policy: | Reproduced under a Creative Commons License |
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