Enantioselective Total Synthesis of (−)-Zygadenine
Yinliang Guo, Jia‐Tian Lu, Runting Fang, Yang Jiao, Jiaqi Liu, Tuoping Luo
Abstract
The Veratrum alkaloids are highly complex steroidal alkaloids characterized by their intricate structural and stereochemical features and exhibit a diverse range of pharmacological activities. A new synthetic pathway has been developed to access this family of natural products, which enabled the first total synthesis of (−)-zygadenine. This synthetic route entails the construction of a hexacyclic carbon skeleton through a stereoselective intramolecular Diels–Alder reaction, followed by a radical cyclization. Subsequently, a meticulously designed sequence of redox manipulations was optimized to achieve the de novo synthesis of this highly oxidized Veratrum alkaloid.
Topics & Concepts
ChemistryEnantioselective synthesisTotal synthesisStereochemistryOrganic chemistryCatalysisChemical synthesis and alkaloidsAxial and Atropisomeric Chirality SynthesisCarbohydrate Chemistry and Synthesis