Tetrahedron Letters

Synthesis of (±)-senoxepin-the first naturally occurring anti-hückel oxepin derivative

A Cleve, F Bohlmann

Index: Cleve, A.; Bohlmann, F. Tetrahedron Letters, 1989 , vol. 30, # 10 p. 1241 - 1244

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Citation Number: 6

Abstract

Abstract The first total synthesis of (±)-senoxepin3 is described. 3 is prepared via an intramolecular [4+ 2] cycloaddition from a substituted decadienyne7. The resulting hexalin8 was converted to a lactone, which on epoxidation, NBS bromination and elimination with NaI afforded senoxepin.