title: Synthesis of diversely functionalized indolizidinones and related bicyclic lactams using intramolecular Grubbs olefin metathesis and Dieckmann condensation.
abstract: 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.
authors.affiliation: Department of Chemistry, Université de Montréal, C. P. 6128, Succ. Centre-Ville, Montréal, P. Q., Canada H3C 3J7. stephen.hanessian@umontreal.ca
authors.forename: Stephen
authors.initials: S
authors.lastname: Hanessian
authors.forename: Helen
authors.initials: H
authors.lastname: Sailes
authors.forename: Alexander
authors.initials: A
authors.lastname: Munro
authors.forename: Eric
authors.initials: E
authors.lastname: Therrien