Ring contraction through epoxide rearrangement: A formal synthesis of capsorubin

Article abstract of DOI:10.1080/00397910008086973

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.

Full text of DOI:10.1080/00397910008086973

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Synthetic Communications: An
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Ring Contraction Through
Epoxide Rearrangement: A
Formal Synthesis of Capsorubin
Mauricio Gomes Constantino a , Paulo Marcos Donate
a , Daniel Frederico a , Tecia Vieira Carvalho a , Luiz
Eduardo Cardoso a & Julio Zukerman-Schpector b
a 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:
b Departamento de Química , Centro de Ciéncias e
Tecnologia, Universidade Federal de Säo Carlos , P.
O. Box 676, 13565--905, Säo Carlos, SP, Brazil
Published online: 04 Dec 2007.
To cite this article: Mauricio Gomes Constantino , Paulo Marcos Donate , Daniel
Frederico , Tecia Vieira Carvalho , Luiz Eduardo Cardoso & Julio Zukerman-
Schpector (2000) Ring Contraction Through Epoxide Rearrangement: A Formal
Synthesis of Capsorubin, Synthetic Communications: An International Journal for
Rapid Communication of Synthetic Organic Chemistry, 30:18, 3327-3340, DOI:
10.1080/00397910008086973
To link to this article: http://dx.doi.org/10.1080/00397910008086973
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