Stereoselective synthesis of erythronolide A via nitrile oxide cycloadditions and related studies.
An expeditious synthesis of erythronolide A is documented. Key steps of the approach include two magnesium-mediated nitrile oxide cycloadditions, a chelation-controlled Grignard reaction, and a Sharpless asymmetric dihydroxylation.
Laboratorium für Organische Chemie, ETH Hönggerberg, Wolfgang Pauli Strasse 10, CH-8093 Zürich, Switzerland.
Dieter
D
Muri
Erick M
EM
Carreira
D003500:Cyclization; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D008968:Molecular Conformation; D009570:Nitriles / Q000737:chemistry*; D010087:Oxides / Q000737:chemistry*; D013237:Stereoisomerism
D009570:Nitriles; D010087:Oxides; C038316:erythronolide A; D004917:Erythromycin