Syntheses of C12,N13 heterocyclic bridged fused indenopyrrolocarbazoles.
Tandem alkylation/cyclization of indenopyrrolocarbazole 4a, a C12 carbon analogue of indolocarbazole K252c, was carried out by general solid-phase and solution-phase methods. Alkylation of fused pyrroloindenylcarbazole 4a derivatives with appropriate monoacetals of diketones afforded the corresponding C12-substituted acetal alcohols. Acid-catalyzed cyclization of these adducts yielded C12,N13-bridged tetrahydrofuran, pyran, and dioxane compounds 10-13.
Underiner
Ted L
TL
Department of Medicinal Chemistry, Cephalon, Inc., 145 Brandywine Parkway, West Chester, Pennsylvania 19380, USA. tunderin@cephalon.com
Mallamo
John P
JP
Singh
Jasbir
J