New entry to convertible isocyanides for the Ugi reaction and its application to the stereocontrolled formal total synthesis of the proteasome inhibitor omuralide.
The development of a new convertible isocyanide, indole-isocyanide, for ready access to pyroglutamic acids culminated in the formal total synthesis of the proteasome inhibitor omuralide featuring a stereocontrolled Ugi reaction. Indole-isocyanide was named after the facilitation of hydrolysis of the resulting 2-(2,2-dimethoxyethyl)anilide via an N-acylindole intermediate obtained by the Ugi multicomponent condensation reaction followed by the indole formation.
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, Mail Code 0343, La Jolla, California 92093-0343, USA.
Cynthia B
CB
Gilley
Matthew J
MJ
Buller
Yoshihisa
Y
Kobayashi
D003486:Cyanides / Q000737:chemistry*; D007211:Indoles / Q000737:chemistry*; D007783:Lactones / Q000138:chemical synthesis* / Q000737:chemistry; D015394:Molecular Structure; D009842:Oligopeptides / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D003486:Cyanides; D007211:Indoles; D007783:Lactones; D009842:Oligopeptides; C090535:benzyloxycarbonyl-isoleucyl-glutamyl(O-tert-butyl)-alanyl-leucinal; C117645:omuralide