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

文献情報

出版日 2020-06-09

DOI 10.1039/D0QO00424C

インパクトファクター 5.281

著者

Zhengwei Ding, Zhi Liu, Guanghu Tong, Linlin Hu, Yangqing He, Yueyun Bao, Zhouhang Lei, Hailong Zhang

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要旨

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.

掲載誌

Organic Chemistry Frontiers

CiteScore: 7.8

自己引用率: 8.7%

年間論文数: 724

Organic Chemistry Frontiers publishes high-quality research from across organic chemistry. Emphases are placed on studies that make significant contributions to the field of organic chemistry by reporting either new or significantly improved protocols or methodologies. Topics include, but are not limited to the following: Organic synthesis Development of synthetic methodologies Catalysis Natural products Functional organic materials Supramolecular and macromolecular chemistry Physical and computational organic chemistry

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

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