Messer Roland, Schmitz Andrea, Moesch Luzia, Häner Robert
Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland.
J Org Chem. 2004 Nov 26;69(24):8558-60. doi: 10.1021/jo048351+.
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.
报道了类天然产物三环化合物的构建。从D-(-)-核糖衍生的二氢呋喃开始，通过分子内杂环狄尔斯-阿尔德反应制备三环骨架。如基于产物的X射线结构分析所确定的，该反应通过内型过渡态以非常高的非对映选择性进行。还描述了所得产物的进一步修饰和衍生化。
