Stereoselective isomerization of 10-arylsulfenate-11,12- dehydroretinoids to 9-cis-retinoids

Article abstract of DOI:10.1016/S0040-4039(98)00810-7

The C₇-C₁₂ triene fragment of 9-cis-retinoids 8 was stereoselectively generated by treatment of propargylic alcohol 3 with phenylsulfenyl chloride/triethylamine at -78 °C, followed by stereospecific reduction of the resulting vinylsulfoxide (t-BuLi, MeLi, MeOH, -78 °C). Thus, 9-cis- retinoic acid 2, the natural ligand of the retinoid X receptor (RXR) was straightforwardly synthesized from 8 in two steps.