title: Elaboration of D-(-)-ribose into a tricyclic, natural product-like scaffold.
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.
authors.affiliation: Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
authors.forename: Roland
authors.initials: R
authors.lastname: Messer
authors.forename: Andrea
authors.initials: A
authors.lastname: Schmitz
authors.forename: Luzia
authors.initials: L
authors.lastname: Moesch
authors.forename: Robert
authors.initials: R
authors.lastname: Häner
mesh_terms: D018360:Crystallography, X-Ray; D005663:Furans / Q000737:chemistry*; D008968:Molecular Conformation; D011108:Polymers / Q000138:chemical synthesis*; D012266:Ribose / Q000138:chemical synthesis / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D005663:Furans; D011108:Polymers; D012266:Ribose