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

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-lactami...

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Bibliographic Details
Published inSynlett Vol. 26; no. 6; pp. 815 - 819
Main Authors Grover, Huck K., Kerr, Michael A.
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.04.2015
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
ENANTIOSELECTIVE SYNTHESIS
heterocycles
natural product
REACTIVITY
piperidine
quebrachamine
INDOLE ALKALOIDS
alkaloid
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Summary: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.
ISSN:0936-5214
1437-2096
DOI:10.1055/s-0034-1379986