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Synlett 2015; 26(16): 2199-2215
DOI: 10.1055/s-0034-1381047
DOI: 10.1055/s-0034-1381047
account
Total Synthesis of Desmethyl Macrolide Antibiotics
Further Information
Publication History
Received: 13 April 2015
Accepted after revision: 09 June 2015
Publication Date:
03 September 2015 (online)
Dedicated to the memory of Dr. Tapas Paul (1976–2012). ‘Chemistry creates its object.’ – Marcelin Berthelot (1860)
Abstract
Macrolide antibiotics occupy a special place in the history of organic chemistry and medicine. This account chronicles the evolution of our approach that ultimately led to the successful total syntheses of four desmethyl (i.e., Me → H) analogues of telithromycin, a semisynthetic derivative of the flagship macrolide antibiotic, erythromycin.
1 Introduction
2 Project Rationale and Retrosynthetic Analysis
3 Lessons Learned from the Total Synthesis of 4,8,10-Tridesmethyl Telithromycin
4 Total Synthesis of 4,10-Didesmethyl Telithromycin
5 Total Synthesis of 4,8-Didesmethyl Telithromycin
6 Total Synthesis of 4-Desmethyl Telithromycin
7 Biological Evaluation of Desmethyl Telithromycin Analogues
8 Concluding Remarks
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