title: Direct stereocontrolled synthesis of polyoxygenated hydrobenzofurans and hydrobenzopyrans from p-peroxy quinols.
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.
authors.affiliation: Departamento de Química Orgánica (C-I), Universidad Autónoma de Madrid, Cantoblanco, 28049-Madrid, Spain.
authors.forename: Silvia
authors.initials: S
authors.lastname: Barradas
authors.forename: M Carmen
authors.initials: MC
authors.lastname: Carreño
authors.forename: Marcos
authors.initials: M
authors.lastname: Gonzalez-López
authors.forename: Alfonso
authors.initials: A
authors.lastname: Latorre
authors.forename: Antonio
authors.initials: A
authors.lastname: Urbano
mesh_terms: D001572:Benzofurans / Q000138:chemical synthesis* / Q000737:chemistry; D001578:Benzopyrans / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D020650:Combinatorial Chemistry Techniques; D018360:Crystallography, X-Ray; D006873:Hydroquinones / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D013237:Stereoisomerism
chemical_list: D001572:Benzofurans; D001578:Benzopyrans; D006873:Hydroquinones; C525723:cleroindicin D