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  • Title: Elaboration of D-(-)-ribose into a tricyclic, natural product-like scaffold.
    Author: Messer R, Schmitz A, Moesch L, Häner R.
    Journal: J Org Chem; 2004 Nov 26; 69(24):8558-60. PubMed ID: 15549845.
    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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