Journal of Organic Chemistry p. 649 - 652 (1984)
Update date:2022-08-05
Topics:
Lewin, Anita H.
Rector, Douglas H.
Parker, Steven R.
Wani, Mansukh C.
Carroll, F. Ivy
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.
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