Total Synthesis of (−)-Batrachotoxinin A: A Local-Desymmetrization Approach
Yinliang Guo, Zhixian Guo, Jia‐Tian Lu, Runting Fang, Si‐Cong Chen, Tuoping Luo
Abstract
An enantioselective total synthesis of (-)-batrachotoxinin A is accomplished based on a key photoredox coupling reaction and the subsequent local-desymmetrization operation. After the expedient assembly of the highly oxidized steroid skeleton, a delicate sequence of redox manipulations was carried out to deliver a late-stage intermediate on gram scale-and ultimately (-)-batrachotoxinin A in an efficient manner.
Topics & Concepts
DesymmetrizationChemistryEnantioselective synthesisTotal synthesisRedoxSkeleton (computer programming)Sequence (biology)Combinatorial chemistryStereochemistryOrganic chemistryCatalysisBiochemistryComputer scienceProgramming languageMarine Sponges and Natural ProductsTraditional and Medicinal Uses of AnnonaceaeAlkaloids: synthesis and pharmacology