Total synthesis of azithromycin.
The quaternary king: Azithromycin (1), which has improved pharmacological profiles compared with erythromycins, was the target of an enantioselective synthesis. All the stereogenic quaternary carbon centers were elaborated by a desymmetrization of 2-substituted glycerols using a chiral imine/CuCl(2) catalyst.
Kim
Hyoung Cheul
HC
Department of Chemistry, School of Molecular Science (BK21), KAIST, Daejeon 305-701, Korea.
Kang
Sung Ho
SH
D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry; D017963:Azithromycin / Q000138:chemical synthesis* / Q000737:chemistry; D002384:Catalysis; D003300:Copper / Q000737:chemistry; D004917:Erythromycin / Q000737:chemistry; D007097:Imines / Q000737:chemistry; D013237:Stereoisomerism
D000900:Anti-Bacterial Agents; D007097:Imines; D004917:Erythromycin; D003300:Copper; D017963:Azithromycin