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Issue 22, 2019
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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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Article information


Submitted
08 Sep 2019
Accepted
30 Sep 2019
First published
02 Oct 2019

Org. Chem. Front., 2019,6, 3781-3785
Article type
Research Article

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, 6, 3781
DOI: 10.1039/C9QO01111K

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