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Synfacts 2010(3): 0259-0259
DOI: 10.1055/s-0029-1219247
DOI: 10.1055/s-0029-1219247
Synthesis of Natural Products and Potential Drugs
© Georg Thieme Verlag
Stuttgart ˙ New York
Synthesis of Vinigrol
T. J. Maimone, J. Shi, S. Ashida, P. S. Baran*
The Scripps Research Institute, La Jolla, USA
Further Information
Publication History
Publication Date:
18 February 2010 (online)
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.