AN EXPEDIENT STEREOCONTROLLED SYNTHESIS OF 7-CIS-RETINOIDS

Abstract

Ethyl (7Z)–retinoate 5 has been efficiently synthesized using as keystep the Suzuki coupling of an in situ generated alkenylboronic acid and the geometrically homogeneous tetraenyliodide with (Z)-geometry, itself obtained by yodomethylenation according to Stork's conditions. Functional group manipulation then afforded (7Z)–retinal 7.

ACKNOWLEDGMENTS

We thank MEC (SAF98-0143) and Xunta de Galicia (PGIDT99PX30105B) for financial support, and Dr. M. Klaus (Hoffmann-La Roche, Basel) for a generous gift of compound 3. We also thank CACTI (Universidade de Vigo) for providing NMR and MS spectra.