Asymmetric synthesis of the fully functionalized six-membered ring of trigoxyphin A. Issue 55 (25th June 2018)

• Record Type: Journal Article
• Authors: Feng, Jing; Yu, Tianzi; Zhang, Zhijiang; Li, Jinpeng; Fu, Shaomin; Chen, Juan; Liu, Bo
• Is Part Of: Chemical communications. Volume 54:Issue 55(2018)
• Page Start: 7665
• Page End: 7668
• Publication Date: 2018-06-25
• Subjects: Chemistry -- Periodicals; 540
• DOI: 10.1039/c8cc04351e
• Languages: English
• ISSNs: 1359-7345

Abstract

Abstract : An asymmetric synthesis strategy of the fully functionalized six-membered ring of trigoxyphin A, a daphnane-type diterpenoid, has been accomplished concisely from ad -tartrate derivative on a multi-gram scale. Abstract : An asymmetric synthesis strategy of the fully functionalized six-membered ring of trigoxyphin A, a daphnane-type diterpenoid, has been accomplished concisely from ad -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.