Synthesis of Vinigrol

Significance

The important biological properties, such as platelet aggregation inhibition, antihypertensive activity, and tumor necrosis factor antagonism, coupled with a high degree of structural complexity have rendered vinigrol a target of widespread interest in the synthetic community. Key transformations in the present approach include a highly selective 1,3-dipolar cycloaddition to give tetracycle C, a Saegusa deamination of bromo­isoxazole E and a Shapiro reaction to complete the carbon skeleton.