Facile synthesis of the daphnane and tigliane framework by semi-flow tube-based-bubbling photooxidation and diastereoselective conjugate addition. Issue 14 (17th June 2020)

• Record Type: Journal Article
• Authors: Ding, Zhengwei; Liu, Zhi; Tong, Guanghu; Hu, Linlin; He, Yangqing; Bao, Yueyun; Lei, Zhouhang; Zhang, Hailong; Li, Pengfei
• Is Part Of: Organic chemistry frontiers. Volume 7:Issue 14(2020)
• Page Start: 1862
• Page End: 1868
• Publication Date: 2020-06-17
• Subjects: Chemistry, Organic -- Periodicals; 547.005
• DOI: 10.1039/d0qo00424c
• Languages: English
• ISSNs: 2052-4110

Abstract

Abstract : The common [5-7-6] tricyclic framework in tigliane and daphnane natural diterpenes containing five contiguous stereocenters has been synthesized in 9 steps from readily available starting materials in a completely stereocontrolled manner. 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.