Stereoselective syntheses of four diastereomers of 3,9,12-trihydroxycalamenene via a benzobicyclo[3.3.1] intermediate.

Sun, Yongquan; Yu, Binxun; Wang, Xiaolei; Tang, Shibing; She, Xuegong; Pan, Xinfu

Sun, Yongquan; Yu, Binxun; Wang, Xiaolei; Tang, Shibing; She, Xuegong; Pan, Xinfu.

Afiliação

Sun Y; State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, Lanzhou, 730000, People's Republic of China.

J Org Chem ; 75(12): 4224-9, 2010 Jun 18.

Article em En | MEDLINE | ID: mdl-20481593

ABSTRACT

ABSTRACT

The highly stereoselective syntheses of four diastereomers of natural 3,9,12-trihydroxycalamenene are described. The syntheses highlight the utility of an unusual framework of benzobicyclo[3.3.1] lactones, which were accomplished via an intramolecular Friedel-Crafts-type Michael addition of alpha,beta-unsaturated lactones.

Assuntos

Compostos Bicíclicos com Pontes/química; Terpenos/síntese química; Lactonas/química; Estrutura Molecular; Sesquiterpenos Policíclicos; Estereoisomerismo; Terpenos/química

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Texto completo: 1 Coleções: 01-internacional Base de dados: MEDLINE Assunto principal: Terpenos / Compostos Bicíclicos com Pontes Idioma: En Revista: J Org Chem Ano de publicação: 2010 Tipo de documento: Article

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