An enantio- and stereocontrolled synthesis of (-)-mycestericin E via cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction.
A new enantiocontrolled synthesis of a potent immunosuppressant(-)-mycestericin E has been accomplished by using cinchona alkaloid-catalyzed asymmetric Baylis-Hillman reaction of an aldehyde with 1,1,1,3,3,3-hexafluoroisopropyl acrylate and Lewis acid-promoted cyclisation of an epoxytrichloroacetimidate as the key steps.
Iwabuchi
Y
Y
Faculty of Pharmaceutical Sciences, Nagasaki University, Nagasaki 852-8521, Japan.
Furukawa
M
M
Esumi
T
T
Hatakeyama
S
S
D020106:Acrylamide / Q000737:chemistry*; D000447:Aldehydes / Q000737:chemistry*; D002384:Catalysis; D002930:Cinchona Alkaloids / Q000737:chemistry*; D005229:Fatty Acids, Monounsaturated / Q000138:chemical synthesis* / Q000737:chemistry; D007700:Kinetics; D009682:Magnetic Resonance Spectroscopy; D010084:Oxidation-Reduction; D010936:Plant Extracts; D013237:Stereoisomerism; D013816:Thermodynamics
D000447:Aldehydes; D002930:Cinchona Alkaloids; D005229:Fatty Acids, Monounsaturated; D010936:Plant Extracts; C087465:mycestericin D; D020106:Acrylamide