Enantioselective Total Synthesis of (-)-Spiroxins A, C, and D
Xin Shu1, Chong-Chong Chen1, Tao Yu1
1Key Laboratory of Synthetic and Natural Functional Molecule Chemistry of the Ministry of Education, College of Chemistry & Materials Science, Northwest University, Xi'an, 710127, China.
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.
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