Tetrahedron p. 3371 - 3386 (1987)
Update date:2022-08-02
Topics:
Suginome, Hiroshi
Yamada, Shinji
We describe a new general method for the synthesis of medium-sized lactones based on ring-enlargement via a regioselective β-scission of alkoxyl radicals generated by photolysis from the hypoiodites of several catacondensed lactols.The syntheses of 9-membered lactones from 6/5 fused lactols, 10-menbered lactones including a naturally occuring lactone, phoracantholide I, from 6/6 or 7/5 fused lactols, and 11-membered lactones from 7/6 or 8/5 fused lactols are shown to be achieved by the present method.This new method may have a potential for application to the synthesis of either smaller or larger-sized lactones.
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