Ring Contraction Through Epoxide Rearrangement: A Formal Synthesis of Capsorubin

Mauricio Gomes Constantino Departamento de Quimica, Faculdade de Filosofia, Ciéncias e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040--901 - Ribeirão Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: [email protected]

Paulo Marcos Donate Departamento de Quimica, Faculdade de Filosofia, Ciéncias e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040--901 - Ribeirão Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: [email protected]

Daniel Frederico Departamento de Quimica, Faculdade de Filosofia, Ciéncias e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040--901 - Ribeirão Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: [email protected]

Tecia Vieira Carvalho Departamento de Quimica, Faculdade de Filosofia, Ciéncias e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040--901 - Ribeirão Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: [email protected]

Luiz Eduardo Cardoso Departamento de Quimica, Faculdade de Filosofia, Ciéncias e Letras de Ribeirão Preto, Universidade de São Paulo, Avenida Bandeirantes 3900, 14040--901 - Ribeirão Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: [email protected]

Julio Zukerman-Schpector Departamento de Química, Centro de Ciéncias e Tecnologia, Universidade Federal de Säo Carlos, P. O. Box 676, 13565--905, Säo Carlos, SP, Brazil

Abstract

An eight-step synthesis of the cyclopentane keto-alcohol 2, which has previously been converted in one step into the carotenoid pigment capsorubin (1), is described. The key step in our synthesis is a stereospecific epoxide rearrangement with ring contraction, thus producing the cyclopentane ring from an epoxide of a cyclohexene.

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Ring Contraction Through Epoxide Rearrangement: A Formal Synthesis of Capsorubin

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Ring Contraction Through Epoxide Rearrangement: A Formal Synthesis of Capsorubin

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