88335-98-2Relevant academic research and scientific papers
SYNTHETIC INVESTIGATIONS IN THE CHEMISTRY OF POLYENE COMPOUNDS. -- XLVIII. STRUCTURE AND TRANSFORMATIONS OF 12-CARBOXYRETINOIC ACIDS AND THEIR ESTERS. SYNTHESIS OF 13-CIS-RETINOIC ACID
Polyachenko, L. N.,Davydova, L. P.,Darskaya, E. N.,Filippova, T. M.,Samokhvalov, G. I.
, p. 685 - 694 (2007/10/02)
In reaction with ethyl β-methylglutaconate under the influence of alkali in methanol the Z and E isomers of β-ionylideneacetaldehyde form isomeric 9Z,11Z,13Z- and 9E,11Z,13Z-12-carboxyretinoic acids.Decarboxylation of the latter in the pyridine-piperidine system in the presence of copper salts leads to 13Z-retinoic acid and is accompanied by the formation of 9,13-dimethyl-7-(1,1,5-trimethyl-5-cyclohexen-6-yl)-7,9,11,13-octatetraene.The stereoisomeric transformations of 12-substituted 9E,Z,11Z,13Z-retinoic acids and the corresponding diols and diacetates obtained from them were investigated.Isomerization takes place at the double bond at the C9 atom and depends on the nature of the substituent at the C12 atom.
Synthesis and Characterization of trans-, 13-cis-, and 11-cis,13-cis-12-(Hydroxymethyl)retinols
Lewin, Anita H.,Rector, Douglas H.,Parker, Steven R.,Wani, Mansukh C.,Carroll, F. Ivy
, p. 649 - 652 (2007/10/02)
Whereas reduction of trans- and 11-cis,13-cis-12-carboxyretinoic acid dimethyl esters gives the trans and 11-cis,13-cis corresponding diols, reduction of 13-cis-12-carboxyretinoic acid dimethyl ester gives essentially no 13-cis diol with trans and 11-cis,13-cis diols being the major products. 12-(Hydroxymethyl)retinol with 13-cis stereochemistry is obtained by reduction of the configurationally locked retinoids 13-cis-12-carboxyretinol δ-lactone and 13-cis-12-(hydroxymethyl)retinoic acid δ-lactone.
