Asymmetric synthesis of the tetrahydropyran ring, C32-C38 fragment, of phorboxazoles |
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Authors: | Brinkmann Yasmin Carreño M Carmen Urbano Antonio Colobert Françoise Solladié Guy |
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Institution: | Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. |
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Abstract: | The asymmetric synthesis of a model aldehyde (2R,6R)-2 and the C32-C38 fragment of phorboxazoles, (2R,4R,6R)-1, is described using a sulfoxide as chiral auxiliary. Key advances include the stereoselective reductions of beta-keto- or beta,gamma-diketosulfoxides, the acid-catalyzed cyclization of enantiopure sulfinyl hydroxy ketone precursors to the tetrahydropyran ring, and the Pummerer reaction on the pendant sulfoxide to create the formyl group. |
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