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.
Gilley
Cynthia B
CB
Department of Chemistry and Biochemistry, University of California, San Diego, 9500 Gilman Drive, Mail Code 0343, La Jolla, California 92093-0343, USA.
Buller
Matthew J
MJ
Kobayashi
Yoshihisa
Y
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