Total Synthesis of (+)‐Alsmaphorazine C and Formal Synthesis of (+)‐Strictamine: A Photo‐Fries Approach
Beiling Gao, Fengjie Yao, Zhaodong Zhang, Hanfeng Ding
Abstract
A bioinspired photo-Fries/imine capture cascade reaction was developed in continuous-flow mode, which facilitated the rapid construction of a series of diversely functionalized 2,7-heterocycle-fused tetrahydrocarbazoles, the ubiquitous core structures embedded in strychnos and akuammiline-type monoterpene indole alkaloids. The synthetic utility of this novel method has been preliminarily explored by the first total synthesis of (+)-alsmaphorazine C and formal synthesis of (+)-strictamine in a concise and efficient manner.
Topics & Concepts
Formal synthesisImineTotal synthesisMonoterpeneContinuous flowIndole testDivergent synthesisCombinatorial chemistryChemistryCascadeStereochemistryOrganic chemistryCatalysisBiochemical engineeringEngineeringChromatographyAlkaloids: synthesis and pharmacologyChemical synthesis and alkaloidsAxial and Atropisomeric Chirality Synthesis