Radical cyclization routes to bridged pyranosides as precursors of densely functionalized cycloalkanes

…, GD Vite, RE McDevitt, B Fraser-Reid

文献索引：Alonso, R. A.; Vite, G. D.; McDevitt, R. E.; Fraser-Reid, B. Journal of Organic Chemistry, 1992 ,  vol. 57,  # 2  p. 573 - 584

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被引用次数: 50

摘要

Glycals derived from hexopyranoses permit the incorporation of iodine at C-2 as well as elaboration of an olefinic residue via the C-5-hydroxymethyl group. Radical cyclization of these functionalities leads to bicyclic systems whose bridge sizes depend on the lengths of the olefinic appendages. Hydrolysis of the anomeric centers of the [2.2. 1] structures leads spontaneously to cyclopentane derivatives. However, with [2.2. 2] structures, the ...