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

Akimori Wada; Fei Wang; Masayoshi Ito

doi:10.1248/cpb.56.112

Notes

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

Akimori Wada, Fei Wang, Masayoshi Ito

著者情報

キーワード: visual pigment, 11Z-3,4-didehydroretinal, diphenyl phosphonate, Horner–Emmons reaction, Z-selectivity

ジャーナルフリー

2008 年 56 巻 1 号 p. 112-114

DOI https://doi.org/10.1248/cpb.56.112

詳細

抄録

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.

責任著者(Corresponding author)

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