Synthesis of Multisubstituted Diazatricyclic Molecules Via Intramolecular Cycloaddition of Cyclic Azomethine Ylides

Diazatricyclic molecules were synthesized from a 4-hydroxyproline derivative. The hydroxy group was transformed into an amino group, onto which an allyl substituent was introduced. Cross-metathesis enabled further substitution on the allyl moiety. Condensation of the resulting 4-aminoproline derivatives with aldehydes generated azomethine ylides that underwent intramolecular cycloaddition to form the tricyclic framework. Functional groups embedded within the tricyclic framework served as handles for further derivatization.