Direct stereocontrolled synthesis of polyoxygenated hydrobenzofurans and hydrobenzopyrans from p-peroxy quinols |
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Authors: | Barradas Silvia Carreño M Carmen Gonzalez-López Marcos Latorre Alfonso Urbano Antonio |
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Institution: | Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain. |
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Abstract: | An acidic-basic tandem catalytic process on p-peroxy quinols with hydroxy alkyl chains at C-4 allowed the one-pot synthesis of hydrobenzofuran and hydrobenzopyran tricyclic epoxides. In this transformation, two new cycles and four new stereogenic centers are created in a highly stereocontrolled manner. The usefulness of the strategy is illustrated with the first total synthesis and structural revision of natural product Cleroindicin D. |
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