Belén Vaz, R. Álvarez, A. Lera
Jul 7, 2016
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Influential Citations
3
Citations
Journal
Tetrahedron
Abstract
Abstract 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.