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Updated: Aug 20, 2026

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Elaboration of D-(-)-ribose into a tricyclic, natural product-like scaffold
Roland Messer1, Andrea Schmitz, Luzia Moesch
1Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Abstract:
The construction of natural product-like, tricyclic compounds is reported. Starting from a D-(-)-ribose-derived dihydrofurane, the tricyclic scaffold is prepared via an intramolecular hetero-Diels-Alder reaction. The reaction proceeds with very high diastereoselectivity through an endo transition state, as established on the basis of X-ray structural analysis of the products. Further modification and derivatization of the obtained products is described.
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