J. Quick et al., PROTEIN-KINASE-C MODULATORS - INDOLACTAMS .1. EFFICIENT AND FLEXIBLE ROUTES FOR THE PREPARATION OF (-)INDOLACTAM-V FOR USE IN THE SYNTHESISOF ANALOGS, Tetrahedron letters, 35(46), 1994, pp. 8549-8552
Three syntheses of the protein kinase C activator, (-)-indolactam V, a
re described and are compared for their potential utility in the prepa
ration of ILV analogs. In one route the 4-amino functionality is intro
duced regiospecifically during the construction of the indole portion
and enantiomeric control is achieved by the alkylation of the amine wi
th a triflate derived from D-valine. One of the routes affords racemic
ILV from which (-)-ILV is obtained by the first reported resolution o
f an indolactam.