Synthesis and Characterization of trans-, 13-cis-, and 11-cis,13-cis-12-(Hydroxymethyl)retinols

Article abstract of DOI:10.1021/jo00178a014

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.