Elaboration of D-(-)-ribose into a tricyclic, natural product-like scaffold.
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.
Messer
Roland
R
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
Schmitz
Andrea
A
Moesch
Luzia
L
Häner
Robert
R
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
D005663:Furans; D011108:Polymers; D012266:Ribose