A convenient and stereoselective synthesis of 11Z-3,4-didehydroretinal by Horner-Emmons reaction using diphenyl phosphonate.
A convenient synthesis of 3,4-didehydroretinal was developed. The Horner-Emmons reaction between 3,4-didehydro-beta-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.
Wada
Akimori
A
Department of Organic Chemistry for Life Science, Kobe Pharmaceutical University, Kobe, Japan. a-wada@kobepharma-u.ac.jp
Wang
Fei
F
Ito
Masayoshi
M
D043844:Crown Ethers / Q000737:chemistry; D015394:Molecular Structure; D009943:Organophosphorus Compounds / Q000737:chemistry*; D012172:Retinaldehyde / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D013237:Stereoisomerism; D014801:Vitamin A / Q000032:analysis / Q000737:chemistry
D043844:Crown Ethers; D009943:Organophosphorus Compounds; D014801:Vitamin A; C017184:dehydroretinal; D012172:Retinaldehyde