Ring Contraction Through Epoxide Rearrangement: A Formal Synthesis of Capsorubin |
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| Authors: | Mauricio Gomes Constantino Paulo Marcos Donate Daniel Frederico Tecia Vieira Carvalho Luiz Eduardo Cardoso Julio Zukerman-Schpector |
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| Institution: | 1. Departamento de Quimica , Faculdade de Filosofia, Ciéncias e Letras de Ribeir?o Preto, Universidade de S?o Paulo , Avenida Bandeirantes 3900, 14040--901 - Ribeir?o Preto-SP, Brazil Phone: +55/16 602 3747 Fax: +55/16 602 3747 E-mail: mgconsta@usp.br;2. Departamento de Química , Centro de Ciéncias e Tecnologia, Universidade Federal de S?o Carlos , P. O. Box 676, 13565--905, S?o Carlos, SP, Brazil |
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| 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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