Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation-Reference-Cited by-同舟云学术

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

Published:2018 Issue:35 Volume:16 Page:6410-6422
ISSN:1477-0520
Container-title:Organic & Biomolecular Chemistry
language:en
Short-container-title:Org. Biomol. Chem.

Author:

Bell Jonathan D.¹²³⁴⁵,Harkiss Alexander H.¹²³⁴⁵,Wellaway Christopher R.⁶⁷⁸⁹^ORCID,Sutherland Andrew¹²³⁴⁵^ORCID

Affiliation:

1. WestCHEM

2. School of Chemistry

3. The Joseph Black Building

4. University of Glasgow

5. Glasgow G12 8QQ

6. Allergic Inflammation Discovery Performance Unit and Respiratory Therapy Area Unit

7. GlaxoSmithKline Medicines Research Centre

8. Stevenage SG1 2NY

9. UK

Abstract

An acid-mediated 6-endo-trig cyclisation has been developed for the synthesis of trans-6-alkyl-2-methyl-4-oxopiperidines and used for the stereoselective preparation of quinolizidine alkaloid, (+)-myrtine and the piperidine alkaloid, (−)-solenopsin A.

Funder

Engineering and Physical Sciences Research Council

GlaxoSmithKline

Publisher

Royal Society of Chemistry (RSC)

Subject

Organic Chemistry,Physical and Theoretical Chemistry,Biochemistry

Link

http://pubs.rsc.org/en/content/articlepdf/2018/OB/C8OB01363B

Reference37 articles.

1. Alkaloids: Chemical and Biological Perspectives , ed. S. W. Pelletier , Pergamon , Oxford, U.K. , 1996 , vol. 10

2. Indolizidine and quinolizidine alkaloids