Modeling a macrocyclic bis[spirodiepoxide] strategy to erythronolide A.
A concise route to functionalized 14-membered macrolides related to erythronolide A was achieved. Key steps include the simultaneous formation of bis[allenic] substrates, efficient macrolactonization, highly stereoselective oxidation to the corresponding bis[spirodiepoxide], and nucleophilic spirodiepoxide opening. The structure and reactivity of these macrolides, and the strategy that led to their evaluation, are discussed.
Ghosh
Partha
P
Department of Chemistry and Chemical Biology, Rutgers, The State University of New Jersey, New Brunswick, New Jersey 08903, USA.
Zhang
Yue
Y
Emge
Thomas J
TJ
Williams
Lawrence J
LJ
D018360:Crystallography, X-Ray; D004852:Epoxy Compounds / Q000737:chemistry*; D004917:Erythromycin / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D047028:Macrocyclic Compounds / Q000737:chemistry*; D008958:Models, Molecular; D015394:Molecular Structure; D010084:Oxidation-Reduction; D013237:Stereoisomerism
D004852:Epoxy Compounds; D047028:Macrocyclic Compounds; C038316:erythronolide A; D004917:Erythromycin