Total syntheses of microminutin and other coumarins through the key intermediate isomurralonginol.

S Allison, SJ Burks, RT Taylor

Index: Allison, Steven; Burks, Steven J.; Taylor, Richard T. Tetrahedron, 1991 , vol. 47, # 47 p. 9737 - 9742

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Citation Number: 4

Abstract

A straightforward route to isomurralonginol (1) from umbelliferone (4 steps, 59% yield) is described. Isomurralonginol is used as the key intermediate in the preparation of isomurralonginol acetate (2)(1 step, 94% yield), murralongin (3)(1 step, 75% yield) and microminutin (2 steps and 38% yield). The synthesis of microminutin involves the selenolactonization of α, β-substituted vinyl acetic acid (12)(50% yield) with spontaneous ...