de novo asymmetric synthesis of daumone via a palladium-catalyzed glycosylation.
The enantioselective syntheses of daumone and two analogues have been achieved in seven to eight steps. This route relies upon a diasteroselective palladium-catalyzed glycosylation reaction for the formation of the anomeric bond. The asymmetry of the sugar and aglycone portion of daumone were introduced by Noyori reduction of an acylfuran and a propargyl ketone. A highly diastereoselective epoxidation and reductive ring opening established the desired C-2 and C-4 stereochemistry of daumone. [reaction: see text]
Guo
Haibing
H
Department of Chemistry, West Virginia University, Morgantown, WV 26506, USA.
O'doherty
George A
GA
D000818:Animals; D017173:Caenorhabditis elegans / Q000737:chemistry; D002384:Catalysis; D005227:Fatty Acids / Q000138:chemical synthesis*; D006031:Glycosylation; D015394:Molecular Structure; D010165:Palladium / Q000737:chemistry*; D010675:Pheromones / Q000138:chemical synthesis*; D013237:Stereoisomerism
D005227:Fatty Acids; D010675:Pheromones; C496586:daumone, C elegans; D010165:Palladium