AUTHOR=Nakamura Akira , Mimaki Kazuki , Tanigami Ken-ichi , Maegawa Tomohiro 

TITLE=An Improved and Practical Method for Synthesizing of α-Sanshools and Spilanthol

JOURNAL=Frontiers in Chemistry

VOLUME=8

YEAR=2020

URL=https://www.frontiersin.org/journals/chemistry/articles/10.3389/fchem.2020.00187

DOI=10.3389/fchem.2020.00187

ISSN=2296-2646

ABSTRACT=<p>An efficient and practical route for the synthesis of α-sanshools and spilanthol is described herein. Several modifications of an existing method enabled the preparation of the (2<italic>E</italic>,6<italic>Z</italic>,8<italic>E</italic>,10<italic>E</italic>)-tetraene precursor of hydroxy-α-sanshool in good yield. A highly selective Wittig reaction employing newly synthesized phosphonium salt with low deliquescence and long-term stability yielded the desired <italic>Z</italic>-form tetraene. This improved methodology was shown to be applicable to the efficient synthesis of α-sanshool and spilanthol.</p>