Asymmetric Total Synthesis of Alstrostine G Utilizing a Catalytic Asymmetric Desymmetrization Strategy.

Zhang, Nanping; Wang, Cheng; Xu, Hailong; Zheng, Ming; Jiang, Huanfeng; Chen, Kai; Ma, Zhiqiang

Zhang, Nanping; Wang, Cheng; Xu, Hailong; Zheng, Ming; Jiang, Huanfeng; Chen, Kai; Ma, Zhiqiang.

Afiliação

Zhang N; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.
Wang C; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.
Xu H; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.
Zheng M; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.
Jiang H; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.
Chen K; College of Chemistry and Chemical Engineering, Central South University, Changsha, 410083, P. R. China.
Ma Z; Key Lab of Functional Molecular Engineering of Guangdong Province, School of Chemistry & Chemical Engineering, South China University of Technology, Wushan Road-381, Guangzhou, 510641, P. R. China.

Angew Chem Int Ed Engl ; 63(34): e202407127, 2024 Aug 19.

Article em En | MEDLINE | ID: mdl-38818628

ABSTRACT

ABSTRACT

A highly effective enantioselective monobenzoylation of 1,3-diols has been developed for the synthesis of 1,1-disubstituted tetrahydro-ß-carbolines. The chemistry has been successfully applied to the asymmetric total synthesis of (+)-alstrostine G, which also features a cascade Heck/hemiamination reaction enabling facile construction of the pivotal pentacyclic core.

Palavras-chave

Desymmetrization; Heck reaction; Monoterpene indole alkaloids; Natural products; Total synthesis

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Texto completo: 1 Base de dados: MEDLINE Idioma: En Ano de publicação: 2024 Tipo de documento: Article

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