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

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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


Submitted
08 Apr 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

Org. Chem. Front., 2020, Advance Article
Article type
Research Article

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, Advance Article , DOI: 10.1039/D0QO00424C

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