Asymmetric Synthesis of (2S,3R)-Capreomycidine and the Total Synthesis of Capreomycin IB

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• 作者：Duane E. DeMong and Robert M. Williams
• 刊名：Journal of the American Chemical Society
• 出版年：2003
• 出版时间：July 16, 2003
• 年：2003
• 卷：125
• 期：28
• 页码：8561 - 8565
• 全文大小：126K
• 年卷期：v.125,no.28(July 16, 2003)
• ISSN：1520-5126

文摘

A 27 step total synthesis of the tuberculostatic macrocyclic peptide antibiotic capreomycin IBhas been accomplished. The synthesis features the use of an enolate-aldimine condensation between achiral glycine aluminum enolate and the benzyl imine of 3-tert-butyldimethylsiloxy-propanal as a means ofpreparing the cyclic guanidine amino acid (2S,3R)-capreomycidine. Additionally, a Hofmann rearrangementwas exacted on a late-stage pentapeptide in order to transform an asparagine residue into a diaminopropanoic acid residue.