An Ugi reaction in the total synthesis of (-)-dysibetaine.
(-)-Dysibetaine has been synthesized in 11 steps from readily available L-malic acid (see scheme). The key step is a unique Ugi 4-center-3-component cyclization reaction, where an ester group acts as the carboxylic acid component. The use of 1,1,1,3,3,3-hexamethyldisilazane as an ammonia equivalent and a specially designed isocyanide leads to an expeditious synthesis.
Isaacson
Jerry
J
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive Mail Code 0343, La Jolla, CA 92093-0343, USA.
Kobayashi
Yoshihisa
Y
D003486:Cyanides / Q000737:chemistry; D003500:Cyclization; D008293:Malates / Q000737:chemistry; D017646:Organosilicon Compounds / Q000737:chemistry; D011760:Pyrrolidinones / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003486:Cyanides; D008293:Malates; D017646:Organosilicon Compounds; D011760:Pyrrolidinones; C431075:dysibetaine; C030298:malic acid; C024548:hexamethylsilazane