1332758-04-9Relevant articles and documents
Total synthesis of pacidamycin D by Cu(I)-Catalyzed oxy enamide formation
Okamoto, Kazuya,Sakagami, Masahiro,Feng, Fei,Togame, Hiroko,Takemoto, Hiroshi,Ichikawa, Satoshi,Matsuda, Akira
supporting information; experimental part, p. 5240 - 5243 (2011/12/14)
The first total synthesis of pacidamycin D, which is expected to be a good candidate as an antibacterial agent against P. aeruginosa, is described. The key elements of our approach feature an efficient and stereocontrolled construction of the Z-oxyvinyl iodide and copper-catalyzed crosscoupling with the tetrapeptide carboxamide.
Stereoselective synthesis of uridine-derived nucleosyl amino acids
Spork, Anatol P.,Wiegmann, Daniel,Granitzka, Markus,Stalke, Dietmar,Ducho, Christian
experimental part, p. 10083 - 10098 (2012/02/05)
Novel hybrid structures of 5′-deoxyuridine and glycine were conceived and synthesized. Such nucleosyl amino acids (NAAs) represent simplified analogues of the core structure of muraymycin nucleoside antibiotics, making them useful synthetic building blocks for structure-activity relationship (SAR) studies. The key step of the developed synthetic route was the efficient and highly diastereose-lective asymmetric hydrogenation of didehydro amino acid precursors toward protected NAAs. It was anticipated that the synthesis of unprotected muraymycin derivatives via this route would require a suitable intermediate protecting group at the N-3 of the uracil base. After initial attempts using PMB- and BOM-N-3 protection, both of which resulted in problematic deprotection steps, an N-3 protecting group-free route was envisaged. In spite of the pronounced acidity of the uracil-3-NH, this route worked equally efficient and with identical stereoselectivities as the initial strategies involving N-3 protection. The obtained NAA building blocks were employed for the synthesis of truncated 5′-deoxymuraymycin analogues (Figure presented).
