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Total Synthesis of the Antibiotic Kendomycin: A Macrocyclization Using the Tsuji-Trost Etherification.
- Source :
-
Angewandte Chemie . Apr2014, Vol. 126 Issue 16, p4297-4300. 4p. - Publication Year :
- 2014
-
Abstract
- 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. [ABSTRACT FROM AUTHOR]
Details
- Language :
- English
- ISSN :
- 00448249
- Volume :
- 126
- Issue :
- 16
- Database :
- Academic Search Index
- Journal :
- Angewandte Chemie
- Publication Type :
- Academic Journal
- Accession number :
- 95563995
- Full Text :
- https://doi.org/10.1002/ange.201400305