Synlett 2015; 26(06): 815-819
DOI: 10.1055/s-0034-1379986
letter
© Georg Thieme Verlag Stuttgart · New York

The Synthesis of 5,5-Disubstituted Piperidinones via a Reductive Amination–Lactamization Sequence: The Formal Synthesis of (±)-Quebrachamine

Huck K. Grover
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada   eMail: makerr@uwo.ca
,
Michael A. Kerr*
Department of Chemistry, The University of Western Ontario, London, ON, N6A 5B7, Canada   eMail: makerr@uwo.ca
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Publikationsverlauf

Received: 08. Oktober 2014

Accepted after revision: 18. Dezember 2014

Publikationsdatum:
05. Februar 2015 (online)


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Abstract

A preliminary investigation into the prospect of a common synthetic intermediate for the synthesis of a variety of indole alkaloids has led to a synthesis of substituted piperidinones and the corresponding piperidines. These common natural product cores are accessed via a reductive amination–lactamization sequence of dimethyl 3-ethyl-3-formylpimelate. The synthetic utility of this initial study has been displayed in the formal synthesis of (±)-quebrachamine.

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