Transformation of D-(-)-ribose into a natural product-like scaffold via a Lewis acid catalyzed intramolecular hetero-Diels-Alder reaction.

Roland Messer, Cyril A Fuhrer, Robert Häner

Index: Nucleosides Nucleotides Nucleic Acids 26(6-7) , 701-4, (2007)

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Abstract

Starting from D-(-)-ribose, a tricyclic natural product-like scaffold suitable for combinatorial derivatization was synthesized via an intramolecular hetero-Diels-Alder reaction. Lithium perchlorate was found to enhance the reaction rate and, at the same time, had a pronounced influence on the chemoselectivity of the reaction. The stereochemical course of the reaction, however, was not influenced by the Lewis acid.