Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation

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:Sutherland, Dr Andrew and Harkiss, Mr Alexander and Bell, Mr Jonathan
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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Project CodeAward NoProject NamePrincipal InvestigatorFunder's NameFunder RefLead Dept
608951Engineering and Physical Sciences Doctoral Training Grant 2012-16Mary Beth KneafseyEngineering and Physical Sciences Research Council (EPSRC)EP/K503058/1VPO VICE PRINCIPAL RESEARCH & ENTERPRISE
722351Sutherland ICASE 2015 (GSK)Andrew SutherlandEngineering and Physical Sciences Research Council (EPSRC)EP/N509176/1CHEM - CHEMISTRY