Catalytic Asymmetric Construction of &#945;-Quaternary Cyclopentanones and Its Application to the Syntheses of (-)-1,14-Herbertenediol and (-)-Aphanorphine.

Zhu, Dao-Yong; Xu, Ming-Hui; Tu, Yong-Qiang; Zhang, Fu-Min; Wang, Shao-Hua

Catalytic Asymmetric Construction of α-Quaternary Cyclopentanones and Its Application to the Syntheses of (-)-1,14-Herbertenediol and (-)-Aphanorphine.

Zhu, Dao-Yong; Xu, Ming-Hui; Tu, Yong-Qiang; Zhang, Fu-Min; Wang, Shao-Hua.

Afiliación

Zhu DY; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.âR. China), Fax: (+86) 931-8912582.
Xu MH; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.âR. China), Fax: (+86) 931-8912582.
Tu YQ; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.âR. China), Fax: (+86) 931-8912582. tuyq@lzu.edu.cn.
Zhang FM; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.âR. China), Fax: (+86) 931-8912582.
Wang SH; State Key Laboratory of Applied Organic Chemistry & College of Chemistry and Chemical Engineering, Lanzhou University, Lanzhou and Collaborative Innovation Center of Chemical Science and Engineering, Tianjin (P.âR. China), Fax: (+86) 931-8912582. wangshh@lzu.edu.cn.

Chemistry ; 21(44): 15502-5, 2015 Oct 26.

Article en En | MEDLINE | ID: mdl-26387785

ABSTRACT

ABSTRACT

A novel and efficient strategy to build α-benzylic quaternary cyclopentanones with excellent enantioselectivities (up to 96 %âee) and high yields (up to 99 % yield) has been developed, and its application demonstrated by the first catalytic asymmetric total synthesis of (-)-1,14-herbertenediol and the formal synthesis of (-)-aphanorphine.

Palabras clave

asymmetric synthesis; enantioselectivity; organocatalysis; quaternary stereocenters; sesquiterpenes

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Texto completo: 1 Bases de datos: MEDLINE Idioma: En Revista: Chemistry Asunto de la revista: QUIMICA Año: 2015 Tipo del documento: Article