Total Synthesis of (−)-Muraymycin D2 and Its Epimer

• Published in: Journal of organic chemistry Vol. 75; no. 5; pp. 1366 - 1377
• Main Authors: Tanino, Tetsuya, Ichikawa, Satoshi, Shiro, Motoo, Matsuda, Akira
• Format: Journal Article
• Language: English
• Published: WASHINGTON American Chemical Society 05.03.2010; Amer Chemical Soc
• Subjects: Anti-Bacterial Agents - chemical synthesis; Anti-Bacterial Agents - chemistry; Carbohydrates. Nucleosides and nucleotides; Catalysis; Catalysts: preparations and properties; Chemistry; Chemistry, Organic; Chromatography, High Pressure Liquid; Crystallography, X-Ray; Dipeptides - chemical synthesis; Dipeptides - chemistry; Exact sciences and technology; General and physical chemistry; Imines - chemistry; Nucleosides - chemical synthesis; Nucleosides - chemistry; Nucleosides, nucleotides and oligonucleotides; Organic chemistry; Peptides - chemical synthesis; Peptides - chemistry; Physical Sciences; Preparations and properties; Science & Technology; Stereoisomerism; Theory of reactions, general kinetics. Catalysis. Nomenclature, chemical documentation, computer chemistry; MULTICOMPONENT REACTIONS; ASYMMETRIC-SYNTHESIS; BAD BUGS; ONE-POT SYNTHESIS; NATURAL-PRODUCTS; DRUGS; ANTIBACTERIAL; CORE STRUCTURE; C-H AMINATION; PEPTIDOGLYCAN BIOSYNTHESIS INHIBITORS; Separation; Peptides; Ugi reaction; Epimer; Deprotection; Acetolysis; HPLC chromatography; Alcohol; Nitrene; Selectivity; Desulfonylation; Amine; Rhodium Complexes; Carboxylic acid; Nucleoside; Ureas; Oxidation; Chemical synthesis; Protection; Guanidines; Natural compound; Total synthesis; Organic amidosulfate; Cyclization; Cyclic compound; Analog; Dipeptides; Antibacterial agent; Isocyanide; Catalyst; Diastereomer; Mercury Bromides

Full details of the first total synthesis of (−)-muraymycin (MRY) D2 and its epimer, the antibacterial nucleoside natural product, are described. Key strategic elements of the approach include the preparation of the urea dipeptide moiety found in the muraymycins containing an l-epi-capreomycidine vi...