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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.

A method for the C-alkylation of 4-nitroindole at the 5 and 7 positions by alkyl Grignard reagents has been developed. The 4-nitro-7-octylindole thus prepared has been used as a starting material for the synthesis of the lyngbyatoxin analog, (-)-7-octylindolactam V.

A synthesis of the macrolide 17-O-methyllythridine is reported in which cyclization is initiated by fluorodesilylation of a trimethlsilylacetate.

The total synthesis of the Lunaria alkaloid codonocarpine is described. Regiospecific formation of the macrocycle is achieved by the use of a properly protected spermidine unit.