Synthesis of the 6,6,5,7-tetracyclic core of daphnilongeranin B

Xiaochun Xiong; Yong Li; Zhaoyong Lu; Ming Wan; Jun Deng; Shuhang Wu; Huawu Shao; Ang Li

doi:10.1039/C3CC47873D

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Synthesis of the 6,6,5,7-tetracyclic core of daphnilongeranin B†

Xiaochun Xiong,‡^abc Yong Li,‡^b Zhaoyong Lu,^b Ming Wan,^b Jun Deng,^b Shuhang Wu,^b Huawu Shao*^a and Ang Li*^b

Author affiliations

* Corresponding authors

^a Natural Products Research Centre, Chengdu Institute of Biology, Chinese Academy of Sciences, Chengdu 610041, China
E-mail: shaohw@cib.ac.cn

^b State Key Laboratory of Bioorganic and Natural Products Chemistry, Shanghai Institute of Organic Chemistry, Chinese Academy of Sciences, 345 Lingling Road, Shanghai 200032, China
E-mail: ali@sioc.ac.cn

^c University of Chinese Academy of Sciences, Beijing 100049, China

Abstract

An efficient approach toward the synthesis of the 6,6,5,7-tetracyclic core of the daphnilongeranin B, a Daphniphyllum alkaloid, is reported. The bridged 6,6-bicyclic system was constructed using a gold(I) catalysed Conia-ene reaction, while the 5- and 7-membered rings were assembled by two diastereoselective Michael addition reactions, respectively.

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DOI: https://doi.org/10.1039/C3CC47873D
Article type: Communication
Submitted: 14 oct. 2013
Accepted: 11 déc. 2013
First published: 12 déc. 2013

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Chem. Commun., 2014,50, 5294-5297

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Synthesis of the 6,6,5,7-tetracyclic core of daphnilongeranin B

X. Xiong, Y. Li, Z. Lu, M. Wan, J. Deng, S. Wu, H. Shao and A. Li, Chem. Commun., 2014, 50, 5294 DOI: 10.1039/C3CC47873D

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Chemical Communications

Synthesis of the 6,6,5,7-tetracyclic core of daphnilongeranin B†

Abstract

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Synthesis of the 6,6,5,7-tetracyclic core of daphnilongeranin B

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