Enantioselective synthesis of (+)- and (-)-dihydroepiepoformin and (+)-epiepoformin |
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Authors: | Carreño M Carmen Merino Estíbaliz Ribagorda María Somoza Alvaro Urbano Antonio |
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Affiliation: | Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049 Madrid, Spain. carmen.carrenno@uam.es |
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Abstract: | [reaction: see text] 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 beta-hydroxy sulfoxide moiety of advanced intermediates to the corresponding sulfone. |
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