Synthesis and biological evaluation of himanimide C and unnatural analogues.
Recently isolated himanimide C (1) can be prepared via a short, flexible, and stereoselective synthesis using a copper-mediated tandem vicinal difunctionalization of dimethyl acetylenedicarboxylate (DMAD, 8) as a key step. The flexibility of the synthesis is exemplified by the preparation of new unnatural himanimide analogues in order to investigate the fungicidal potency of this new family. [structure: see text]
Sellès
Patrice
P
Research Chemistry, SYNGENTA Crop Protection AG, CH-4002 Basel, Switzerland. patrice.selles@syngenta.com
D000114:Acetylene / Q000031:analogs & derivatives* / Q000737:chemistry; D000480:Alkynes; D001487:Basidiomycota / Q000737:chemistry; D001897:Boronic Acids; D003500:Cyclization; D019811:Hydroxylamine; D008958:Models, Molecular; D008968:Molecular Conformation; D011758:Pyrroles / Q000138:chemical synthesis*; D013329:Structure-Activity Relationship
D000480:Alkynes; D001897:Boronic Acids; D011758:Pyrroles; C511646:himanimide C; D019811:Hydroxylamine; C022918:acetylenedicarboxylic acid dimethyl ester; D000114:Acetylene