Paul E. Driedger

Protein kinase C modulators. Indolactams. 1. Efficient and flexible routes for the preparation of (-)-indolactam V for use in the synthesis of analogs

Abstract Three syntheses of the protein kinase C activator, (-)-indolactam V, are described and are compared for their potential utility in the preparation of ILV analogs. In one route the 4-amino functionality is introduced regiospecifically during the construction of the indole portion and enantiomeric control is achieved by the alkylation of the amine with a triflate derived from d -valine. One of the routes affords racemic ILV from which (-)-ILV is obtained by the first reported resolution of an indolactam.