Synlett 2012; 23(17): 2564-2566
DOI: 10.1055/s-0032-1317172
letter
© Georg Thieme Verlag Stuttgart · New York

Synthesis of Hydroxy-α-sanshool

Bo Wu
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China   Fax: +852(2)8571586   eMail: phtoy@hku.hk
,
Kun Li
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China   Fax: +852(2)8571586   eMail: phtoy@hku.hk
,
Patrick H. Toy*
Department of Chemistry, The University of Hong Kong, Pokfulam Road, Hong Kong, P. R. of China   Fax: +852(2)8571586   eMail: phtoy@hku.hk
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Publikationsverlauf

Received: 03. Juli 2012

Accepted after revision: 03. August 2012

Publikationsdatum:
13. September 2012 (online)


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Abstract

The amide hydroxy-α-sanshool is responsible for the mild numbing sensation experienced when Sichuan (or Szechuan) peppercorns (huajiao) are eaten. It has been synthesized in six steps from simple commercially available starting materials using Wittig reactions as the key transformations for construction of the carbon skeleton. The penultimate synthetic intermediate was 2E,6Z,8E,10E-dodecatetraenoic acid, and its crystalline nature allowed it, and thus hydroxy-α-sanshool, to be purified to a very high level of stereochemical homogeneity.

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