Stereoselective total synthesis of (+)-myriocin from D-mannose.
The stereoselective total synthesis of myriocin 1 from D-mannose is described; the carbon framework with three contiguous chiral centers including a tetra-substituted carbon with nitrogen was effectively constructed using Overman rearrangement as the key reaction.
Oishi
T
T
Department of Applied Chemistry, Faculty of Science and Technology, Keio University, Hiyoshi, Kohoku-ku, Yokohama 223-8522, Japan.
Ando
K
K
Chida
N
N
D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D007166:Immunosuppressive Agents / Q000138:chemical synthesis* / Q000737:chemistry; D008358:Mannose / Q000737:chemistry*; D008968:Molecular Conformation; D013237:Stereoisomerism
D005229:Fatty Acids, Monounsaturated; D007166:Immunosuppressive Agents; D008358:Mannose; C001996:thermozymocidin