Hydroxy-alpha-sanshool (HAS) is the component of Sichuan peppercorn that is responsible for the numbing/tingling sensation one experiences when eating it, and is a polyunsaturated fatty acid amide.  Research into the biological activity of this compound has been limited due to the difficulty and expense of isolating it from natural sources.  In order to overcome this limitation we have developed a short and efficient synthesis of HAS from simple building blocks such as 4-bromobutanol, sorbaldehyde and isobutylene oxide that utilizes a pair of Wittig reactions as the key transformations for construction of the carbon skeleton of the corresponding carboxylic acid.  A by-product of our route is isomeric hydroxyl-beta-sanshool, which may have similar biological activity to HAS.  Furthermore, we have synthesized related hydroxyl-gamma-sanshool using a highly stereoselective alkyne to diene rearrangement reaction.

Synthesis of hydroxy-alpha-sanshool and related compounds

245th National Meeting (2013)

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