Asymmetric Synthesis of (2S,3R)-Capreomycidine and the Total Synthesis of Capreomycin IB
journal contributionposted on 20.06.2003, 00:00 by Duane E. DeMong, Robert M. Williams
A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin IB has been accomplished. The synthesis features the use of an enolate−aldimine condensation between a chiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means of preparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangement was exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.
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Asymmetric Synthesisbenzyl iminecyclic guanidinechiral glycine aluminum enolateCapreomycidinediaminopropanoic acid residuetertsynthesis featurescapreomycidineHofmann rearrangementpentapeptidecondensationTotal Synthesistuberculostatic macrocyclic peptide antibiotic capreomycin IBasparagine residueCapreomycin IB27 step