Total Synthesis of Vinorine
Shiyuan Kang, Yinxia Wu, Min Hu, Ying Ma, Xiangdi Huang, Zhen Hao, Xiujuan Li, Wen Chen, Hongbin Zhang
Abstract
The asymmetric total synthesis of vinorine, a polycyclic and cage-like alkaloid, has been realized in a flexible approach. Key features of the current synthesis include an aza-Achmatowicz rearrangement/Mannich-type cyclization to install the highly functional 9-azabicyclo-[3.3.1]nonane scaffold, a high yield Fischer indole annulation to synthesize the common intermediate for sarpagine-ajamaline type alkaloids, and an Ireland-Claisen rearrangement to construct the C15-C20 bond.
Topics & Concepts
ChemistryAnnulationNonaneTotal synthesisYield (engineering)StereochemistryClaisen rearrangementIndole testScaffoldCombinatorial chemistryOrganic chemistryCatalysisMaterials scienceMetallurgyBiomedical engineeringMedicineAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsTraditional and Medicinal Uses of Annonaceae