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Chem Pharm Bull (Tokyo). 2008 Mar;56(3):404-6.

A PhSeCl-mediated allylic oxidation of prenyl moiety: a convenient method for the construction of 3-isopenten-2-ol unit.

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  • 1Faculty of Pharmaceutical Sciences, Tokyo University of Science (RIKADAI), 2641 Yamazaki, Noda, Chiba 278-8510, Japan.


A phenylselenenyl chloride (PhSeCl)-mediated allylic oxidation to give allylically rearranged alcohol has been developed. A possible mechanism for the present reaction is generation of allylic selenide from prenyl moiety via [1,3]-sigmatropic rearrangement, followed by oxidation and [2,3]-sigmatropic rearrangement to afford 3-isopenten-2-ol.

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