J. Murga, E. Falomir, M. Carda
Oct 31, 2002
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Influential Citations
12
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Tetrahedron-asymmetry
Abstract
Abstract Protected erythrulose derivatives have been shown to undergo highly stereoselective dicyclohexylboron chloride-mediated aldol reactions. After suitable synthetic manipulation of the resulting aldol adducts, chiral polyoxygenated molecules can be obtained in which either three or all four carbon atoms of the starting erythrulose molecule have been incorporated. Erythrulose derivatives may therefore behave, according to convenience, as chiral, functionalized d 3 or d 4 synthons. As an example, this methodology has been applied to a stereoselective synthesis of the naturally occurring, pharmacologically active lactone (+)-boronolide.