Stereocontrolled synthesis of (S)-9-cis- and (S)-11-cis-13,14-dihydroretinoic acid

Add time:08/23/2019    Source:sciencedirect.com

The 9-cis and 11-cis stereoisomers of 13,14-dihydroretinoic acid with S configuration, (S)-7 and (S)-9, respectively, have been synthesized stereoselectively. The former has been recently characterized as the first endogenous natural ligand of the retinoid X receptor (RXR). The Julia-Kocienski reaction of allyl sulfones and aldehydes was used as connective step and afforded the Z isomer of a trienyl ester accounting for the entire side chain of the targets. A highly selective and unidirectional iodine-induced isomerization of a Z,Z,E triene to the desired E,Z,E isomer was required prior to the synthesis of (S)-7 via a Suzuki cross-coupling. The same approach to (S)-9 led to substantial isomerization when the Suzuki cross-coupling was used as the last bond-forming reaction. As alternative, the two bond-forming steps were exchanged and the synthesis of (S)-9 was completed using the Z-selective Julia-Kocienski reaction.

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