Infoscience

Journal article

"Isoretinol" and retinal: an unorthodox but simple route to the vitamin A series

"Isoretinol" I was prepd. in 55% yield by methylation of II, obtained by reaction of III with the (chlorodihydrofuryl)copper IV. Oxidn. of I with Me2SO contg. N,N'-dicyclohexylcarbodiimide gave a stereoisomeric mixt. of retinal. Similarly, Me2C:CHCH2CH2CMe:CHCH:C:CMeCH2CH2OH was prepd. from geranyl bromide and IV and oxidized to give 4,5-dehydrofarnesal, Me2C:CHCH2CH2CMe:CHCH:CHCMe:CHCHO, which was reduced to give 4,5-dehydrofarnesol, Me2C:CHCH2CH2CMe:CHCH:CHCMe:CHCH2OH. [on SciFinder (R)]

    Keywords: Alkylation (of (chlorodihydrofuryl)copper by ionylideneethyl chloride and geranyl bromide in prepn. of isoretinol and retinal) ; isoretinol; retinal; alkylation ionylideneethyl chloride chlorodihydrofurylcopper

    Note:

    CAN 98:4685 30-40 Terpenes and Terpenoids Inst. Chim. Org.,Univ. Lausanne,Lausanne,Switz. Journal 0044-8249 written in German. 6138-90-5; 55732-70-2 Role: RCT (Reactant), RACT (Reactant or reagent) (alkylation by, of (chlorodihydrofuryl)copper); 83378-78-3 Role: RCT (Reactant), RACT (Reactant or reagent) (ionylideneethylation and geranylation of); 83378-85-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation of); 83378-79-4P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and methylation-ring cleavage of); 74916-02-2P; 83378-80-7P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and oxidn.-isomerization of); 64197-46-2P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn. of); 83378-84-1P Role: RCT (Reactant), SPN (Synthetic preparation), PREP (Preparation), RACT (Reactant or reagent) (prepn. and redn.-isomerization of); 116-31-4P; 472-86-6P; 514-85-2P; 564-87-4P; 23790-80-9P; 67689-12-7P; 67711-05-1P; 74284-77-8P; 83378-81-8P; 83378-82-9P; 83378-83-0P Role: SPN (Synthetic preparation), PREP (Preparation) (prepn. of)

    Reference

    • LSCO-ARTICLE-1982-005

    Record created on 2006-03-03, modified on 2016-08-08

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