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Total Synthesis of the Antibiotic Kendomycin: A Macrocyclization Using the Tsuji–Trost Etherification
Author(s) -
Sengoku Tetsuya,
Xu Shu,
Ogura Kenji,
Emori Yoshinori,
Kitada Kenji,
Uemura Daisuke,
Arimoto Hirokazu
Publication year - 2014
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.201400305
Subject(s) - antibiotics , chemistry , stereochemistry , biochemistry
A highly stereocontrolled, convergent total synthesis of kendomycin [(−)‐TAN2162], an ansa‐macrocyclic antibiotic, is reported. The key of the strategy is an unprecedented Tsuji–Trost macrocyclic etherification, followed by a transannular Claisen rearrangement to construct the 18‐membered carbocyclic framework. The oxa‐six‐ and five‐membered rings were also stereoselectively constructed respectively by a cascade oxidative cyclization at an unfunctionalized benzylic position and using a one‐pot epoxidation/5‐ exo ‐tet epoxide opening.