Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A

Hao Zhang; Shiqiang Ma; Zhimin Xing; Lin Liu; Bowen Fang; Xingang Xie; Xuegong She

doi:10.1039/C7QO00550D

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Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A†

Hao Zhang,^a Shiqiang Ma,^a Zhimin Xing,^a Lin Liu,^a Bowen Fang,^b Xingang Xie

*^a and Xuegong She

*^ac

Author affiliations

* Corresponding authors

^a State Key Laboratory of Applied Organic Chemistry, Department of Chemistry, Lanzhou University, 222 South Tianshui Road, Lanzhou 730000, China
E-mail: xiexg@lzu.edu.cn, shexg@lzu.edu.cn

^b Chemical Engineering Institute, Northwest University for Nationalities, Lanzhou, China

^c Collaborative Innovation Center of Chemical Science and Engineering, Tianjin 3000721, China

Abstract

A tandem radical cyclization reaction towards the 6/6/5 fused tricyclic skeleton, which exists in numerous natural products, was developed in modest to good yields. In this transformation, two C–C bonds and two rings were formed successively via a tandem 5-exo-trig/6-endo-trig cyclization reaction. 5-epi-7-deoxy-Isoabietenin A was also synthesized efficiently via this strategy.

This article is part of the themed collection: Synthetic Approaches to Natural Products via Catalytic Processes

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Article information

DOI: https://doi.org/10.1039/C7QO00550D
Article type: Research Article
Submitted: 04 Jūl. 2017
Accepted: 14 Aug. 2017
First published: 15 Aug. 2017

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Org. Chem. Front., 2017,4, 2211-2215

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Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A

H. Zhang, S. Ma, Z. Xing, L. Liu, B. Fang, X. Xie and X. She, Org. Chem. Front., 2017, 4, 2211 DOI: 10.1039/C7QO00550D

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Organic Chemistry Frontiers

Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A†

Abstract

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Rapid construction of the 6/6/5 tricyclic framework via a tandem radical cyclization reaction and its application to the synthesis of 5-epi-7-deoxy-isoabietenin A

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