Asymmetric total synthesis of botcinins C, D, and F.
Stereoselective total synthesis of botcinins C, D, and F is effectively carried out through asymmetric aldol reactions, 6-endo ring closure, and SmI2-mediated 3,4-trans or -cis stereoselective intramolecular Reformatsky reaction. Rapid esterification of the main skeleton of botcinins with the chiral side chain using MNBA and DMAP produced botcinin D, an antifungal chemical against a pathogen of rice blast disease.
Department of Applied Chemistry, Faculty of Science, Tokyo University of Science, Tokyo, Japan.
Hiroki
H
Fukui
Isamu
I
Shiina
D000935:Antifungal Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D020171:Botrytis / Q000737:chemistry; D020082:Magnaporthe / Q000187:drug effects*; D015394:Molecular Structure; D010935:Plant Diseases / Q000382:microbiology; D011753:Pyrones / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D013237:Stereoisomerism
D000935:Antifungal Agents; D011753:Pyrones; C530928:botcinin C; C530929:botcinin D; C511120:botcinin F