Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition
Literature Information
Publication Date
2020-06-09
DOI
10.1039/D0QO00424C
Impact Factor
5.281
Authors
Zhengwei Ding, Zhi Liu, Guanghu Tong, Linlin Hu, Yangqing He, Yueyun Bao, Zhouhang Lei, Hailong Zhang
View Original
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.
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Source Journal
Organic Chemistry Frontiers
CiteScore:
7.8
Self-citation Rate:
8.7%
Articles per Year:
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
Recommended Compounds
5,7,8'-Trihydroxy-2',2'-dimethyl-2'H,4H-3,6'-bichromen-4-one
CAS Number:
129280-33-7
Molecular Formula:
C20H16O6
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