title: An efficient synthesis of the polar part of sulfamisterin and its analogs.
abstract: An efficient synthesis of the polar part of sulfamisterin and its analogs starting from d-xylose is described. The corresponding allylic thiocyanates and trichloroacetimidates were subjected to aza-Claisen rearrangement that effectively generated a quaternary carbon having an amino group as one of the substituents. Subsequent functional group interconversions afforded the highly functionalized branched aminopolyol 29 that is expected to have the crucial application in the construction of sulfamisterin. On the other hand, the second diastereoisomer 34 would be transformed to 2-epi-congener. With respect to the appropriate stereochemical arrangement, the prepared polar segments 29 and 34 can also be utilized for the synthesis of mycestericins (E, G) and their analogs.
authors.affiliation: Institute of Chemical Sciences, Department of Organic Chemistry, P.J. Šafárik University, Moyzesova 11, Sk-040 01 Košice, Slovak Republic. miroslava.martinkova@upjs.sk
authors.forename: Miroslava
authors.initials: M
authors.lastname: Martinková
authors.forename: Jozef
authors.initials: J
authors.lastname: Gonda
authors.forename: Alena
authors.initials: A
authors.lastname: Uhríková
authors.forename: Jana Špaková
authors.initials: JŠ
authors.lastname: Raschmanová
authors.forename: Juraj
authors.initials: J
authors.lastname: Kuchár
mesh_terms: D060326:Chemistry Techniques, Synthetic / Q000379:methods*; D004791:Enzyme Inhibitors / Q000138:chemical synthesis* / Q000737:chemistry*; D008958:Models, Molecular; D008968:Molecular Conformation; D013110:Sphingosine / Q000031:analogs & derivatives* / Q000138:chemical synthesis / Q000737:chemistry; D014994:Xylose / Q000737:chemistry*
chemical_list: D004791:Enzyme Inhibitors; C497029:sulfamisterin; D014994:Xylose; D013110:Sphingosine