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Issue 35, 2018
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Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation

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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.

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

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Publication details

The article was received on 09 Jun 2018, accepted on 10 Jul 2018 and first published on 11 Jul 2018


Article type: Paper
DOI: 10.1039/C8OB01363B
Citation: Org. Biomol. Chem., 2018,16, 6410-6422
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    Stereoselective synthesis of 2,6-trans-4-oxopiperidines using an acid-mediated 6-endo-trig cyclisation

    J. D. Bell, A. H. Harkiss, C. R. Wellaway and A. Sutherland, Org. Biomol. Chem., 2018, 16, 6410
    DOI: 10.1039/C8OB01363B

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