Issue 14, 2020

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

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

Supplementary files

Article information

Article type
Research Article
Submitted
08 Apr 2020
Accepted
08 Jun 2020
First published
09 Jun 2020

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

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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