Access to 2,6-disubstituted 4-oxopiperidines using a 6-endo-trig cyclization: stereoselective synthesis of spruce alkaloid and (+)-241D

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, Dr Andrew and Harkiss, Mr 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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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