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Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

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Abstract

Nitrone induced 1,3-dipolar [3 + 2] cycloadditions were studied to construct the core structure of Calyciphylline A-type Daphniphyllum alkaloids. This approach is capable of installing the cis-hydroindole A–C ring as well as the spiro-A–C–E ring with the all-carbon quaternary centers at C-5 and C-8, and has been successfully used in the total synthesis of himalensine A. It also lays the foundation for the synthesis of challenging Calyciphylline A-type alkaloids, such as daphniyunnine A.

Graphical abstract: Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

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Publication details

The article was received on 08 Sep 2019, accepted on 30 Sep 2019 and first published on 02 Oct 2019


Article type: Research Article
DOI: 10.1039/C9QO01111K
Org. Chem. Front., 2019, Advance Article

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    Exploration of 1,3-dipolar cycloaddition reactions to construct the core skeleton of Calyciphylline A-type alkaloids

    J. Zhong, H. He and S. Gao, Org. Chem. Front., 2019, Advance Article , DOI: 10.1039/C9QO01111K

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