Abstract

BARRERO, Alejandro F. et al. Regio- and Enantioselective Functionalization of Acyclic Polyprenoidst. J. Mex. Chem. Soc [online]. 2006, vol.50, n.4, pp.149-156. ISSN 1870-249X.

In this paper we present the results obtained in the positional selective functionalization of the double bond located at the terminal isopropylidene unit of acyclic polyprenoids. Studies to introduce the hydroxyl group or related oxygenated functions has been tested using oxidation with SeO₂ or catalytic procedures employing Pd(II) catalysts. This functionalization is usually found in many natural or synthetic acyclic terpenes and would permit to carry out epoxydations regio- and stereoselectives. Furthermore, asymmetric dihydroxilation procedure has been optimized in different polyprenoids in order to generalize this methodology as the key step for the enantioselective synthesis of epoxides.

Keywords : acyclic polyprenes; allylic functionalization; selenium dioxide; palladium; asymmetric dihydroxylation; terpenes.

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