Enantioselective Total Synthesis of (−)‐Spiroxins A, C, and D
Xin Shu, Chong‐Chong Chen, Yu Tao, Jia-Yi Yang, Xiangdong Hu
Abstract
Spiroxins A, C, and D are metabolites that have been identified in the marine fungal strain LL-37H248. Their unique polycyclic structures and intriguing biological activities make them attractive targets for the synthetic community. Based on a scalable enantioselective epoxidation of 5-substituted naphthoquinone, an oxidation/spiroketalization cascade, ortho-selective chlorination of the phenol unit, and oxime-ester-directed acetoxylation, an enantioselective total synthesis of (-)-spiroxins A and C and the first total synthesis of (-)-spiroxin D have been achieved.
Topics & Concepts
Enantioselective synthesisTotal synthesisChemistryPhenolStereochemistryOximeOrganic chemistryCatalysisMicrobial Natural Products and BiosynthesisMarine Sponges and Natural ProductsOxidative Organic Chemistry Reactions