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