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Enantioselective Total Synthesis of (−)‐Spiroxins A, C, and D
Author(s) -
Shu Xin,
Chen ChongChong,
Yu Tao,
Yang Jiayi,
Hu Xiangdong
Publication year - 2021
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.202105921
Subject(s) - enantioselective synthesis , total synthesis , chemistry , phenol , oxime , stereochemistry , organic chemistry , combinatorial chemistry , catalysis
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.