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New carbocyclic retinoids/rexinoids based on terpenes

A series of 9-cis-retinoic acid analogs modified at the hydrophobic ring with a cyclohexenyl moiety derived from natural terpenes has been stereoselectively prepared using a Suzuki cross-coupling as key step to connect alkenyl fragments functionalized as iodide or boronic acid.

For convenience, due to the instability of the iodotetraenyl esters, the sequence is best carried out without isolation of the intermediates. In turn, the boronic acids were obtained by trapping with a borate the alkenyl organolithium intermediate obtained by Shapiro reaction of the hydrazones derived from either naturally-occurring ketones or derivatives thereof.

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Oporto, 1
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