A Convenient and Stereoselective Synthesis of 11Z-3,4-Didehydroretinal by Horner-Emmons Reaction Using Diphenyl Phosphonate

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  • Wada Akimori
    Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University
  • Wang Fei
    Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University
  • Ito Masayoshi
    Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University

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Abstract

A convenient synthesis of 3,4-didehydroretinal was developed. The Horner–Emmons reaction between 3,4-didehydro-β-ionone and diphenyl phosphonate in the presence of crown ether gave the retinonitrile as an isomeric mixture, in which the newly produced double bond was predominantly 11Z-form. After separation of the 11Z-form retinonitrile, it was converted into the corresponding retinal in good yield without isomerization of the double bonds.

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