Issue 55, 2018

Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A

Abstract

An asymmetric synthesis strategy of the fully functionalized six-membered ring of trigoxyphin A, a daphnane-type diterpenoid, has been accomplished concisely from a D-tartrate derivative. Key elements of this synthesis involve the tandem ozonization/intramolecular HWE reaction to construct the α,β-unsaturated cyclohexenone skeleton, the radical cyclization to introduce the C8 chirality and sequential Kumada cross-coupling/hydroboration–oxidation to introduce the C11 chirality. The target substructure could be synthetically achieved on a multi-gram scale.

Graphical abstract: Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A

Supplementary files

Article information

Article type
Communication
Submitted
31 May 2018
Accepted
15 Jun 2018
First published
16 Jun 2018

Chem. Commun., 2018,54, 7665-7668

Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A

J. Feng, T. Yu, Z. Zhang, J. Li, S. Fu, J. Chen and B. Liu, Chem. Commun., 2018, 54, 7665 DOI: 10.1039/C8CC04351E

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