SOLID-PHASE SYNTHESIS OF TROPANE DERIVATIVES

The azabicyclic moiety present in tropane alkaloids can be convenientl y synthesized in high yield on solid phase using a modification of Rob inson's tropinone synthesis.(1) The E-amino group on a lysine residue attached to Tentagel(R) resin was treated with 10 eq excess of succini c dialdehyde and 1 eq of acetonedicarboxylic acid for 12 hours with a citric acid buffer of pH 4 as solvent, resulting in the formation of a n 8-azabicyclo[3.2.1]octane structure on the epsilon-amino group of ly sine in 93% yield. (C) 1998 Elsevier Science Ltd. All rights reserved.