Issue 14, 2020
From the journal:

Organic Chemistry Frontiers

Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition†

Zhengwei Ding,‡a   Zhi Liu,‡a   Guanghu Tong,a   Linlin Hu,b   Yangqing He, ORCID logo *b   Yueyun Bao,a   Zhouhang Lei,a   Hailong Zhangc  and  Pengfei Li ORCID logo *ad  

* Corresponding authors

a Frontier Institute of Science and Technology, Xi'an Jiaotong University, Xi'an, China
E-mail: lipengfei@xjtu.edu.cn

b Department of Applied Chemistry, Xi'an University of Technology, Xi'an 710048, China
E-mail: yqhe6@xaut.edu.cn

c Department of Medicinal Chemistry, School of Pharmacy, Xi'an Jiaotong University, Xi'an, China

d Xi'an Key Laboratory of Sustainable Energy Materials Chemistry, Xi'an Jiaotong University, Xi'an 710049, China

Abstract

The universal [5-7-6] tricyclic framework of tigliane and daphnane diterpenes containing five contiguous stereocenters has been synthesized in 9 steps from readily available starting materials in a completely stereocontrolled manner. This was enabled by designing a semi-flow tube-based bubbling photoreaction setup for an efficient oxidative dearomatization and by devising an open chain remote group-assisted selective 1,4-addition. The results provide a potentially rapid and divergent approach to synthesize various related diterpene molecules.

Graphical abstract: Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition

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Article information

DOI
https://doi.org/10.1039/D0QO00424C
Article type
Research Article
Submitted
08 Apr 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

Org. Chem. Front., 2020,7, 1862-1868

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Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition

Z. Ding, Z. Liu, G. Tong, L. Hu, Y. He, Y. Bao, Z. Lei, H. Zhang and P. Li, Org. Chem. Front., 2020, 7, 1862 DOI: 10.1039/D0QO00424C

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