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CC BY ND NC 4.0 · Synlett 2019; 30(04): 413-416
DOI: 10.1055/s-0037-1611652
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A Short, Efficient, and Stereoselective Synthesis of Piperine and its Analogues

Adriano Bauer ◊
,
Jun-Hyun Nam ◊
,

Funding by the Austrian Research Fund (FWF Project P27194) is gratefully acknowledged.
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Publikationsverlauf

Received: 26. November 2018

Accepted after revision: 16. Dezember 2018

Publikationsdatum:
14. Januar 2019 (online)


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These authors contributed equally to this work

Published as part of the 30 Years SYNLETT – Pearl Anniversary Issue

Abstract

A quantitative synthesis of piperine from commercially available starting material is presented. The synthesis relies on a stereoselective nucleophilic attack of an in situ generated cuprate onto a cyclobutene lactone. The so-formed aryl-substituted cyclobutene spontaneously undergoes a conrotatory 4π-electrocyclic ring opening to form the 4-aryl pentadienoic acid as a single diastereoisomer. The high-yielding synthesis can be easily modulated on the aryl and on the amide moiety for the synthesis of a wide range of piperine analogues.

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