Enantioselective Synthesis of (+) and (-)-Dihydroepiepoformin and (+)-Epiepoformin

Carreño, M. Carmen; Merino, Estíbaliz; Ribagorda, Maria; Somoza, Álvaro; Urbano, Antonio

doi:10.1021/ol050287a

Published March 11, 2005 | Version v1

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Enantioselective Synthesis of (+) and (-)-Dihydroepiepoformin and (+)-Epiepoformin

1. Universidad Autónoma de Madrid

The enantioselective synthesis of both enantiomers of dihydroepiepoformin (1) and (+)-epiepoformin (2) was achieved from (p-tolylsulfinyl)-methyl-p-quinols (SR)- or (SS)-3 and (4R,SR)-4, respectively. Key features include the stereocontrolled conjugate addition of AlMe3 to p-quinol 3 and retrocondensation to the ketone functionality, previous to oxidation of the p-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone

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Accepted: 2005

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Enantioselective Synthesis of (+) and (-)-Dihydroepiepoformin and (+)-Epiepoformin

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