Synthesis of diversely functionalized indolizidinones and related bicyclic lactams using intramolecular Grubbs olefin metathesis and Dieckmann condensation.
Bicyclic 1-aza-2-oxo ring systems with versatile functionality were synthesized from the Grubbs olefin metathesis of appropriate olefinic precursors, starting with l-pyroglutamic acid. The carbocyclization products were further functionalized utilizing the double bond or by enolate chemistry of the corresponding beta,gamma-unsaturated bicyclic lactam. In an alternative strategy, indolizidinones were synthesized by application of an intramolecular Dieckmann cyclization. A constrained peptidomimetic thrombin inhibitor was prepared from one of the bicyclic indolizidinones.
Hanessian
Stephen
S
Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
Sailes
Helen
H
Munro
Alexander
A
Therrien
Eric
E