title: Stereocontrol in a combined allylic azide rearrangement and intramolecular Schmidt reaction.
abstract: Pre-equilibration of an interconverting set of isomeric allylic azides is coupled with an intramolecular Schmidt reaction to afford substituted lactams stereoselectively. The effect of substitution and a preliminary mechanistic study are reported. The synthetic potential of this method is demonstrated in the context of an enantioselective synthesis of an advanced intermediate leading toward pinnaic acid.
authors.affiliation: Department of Medicinal Chemistry, Delbert M. Shankel Structural Biology Center, University of Kansas, 2034 Becker Drive, Lawrence, Kansas 66045, USA.
authors.forename: Ruzhang
authors.initials: R
authors.lastname: Liu
authors.forename: Osvaldo
authors.initials: O
authors.lastname: Gutierrez
authors.forename: Dean J
authors.initials: DJ
authors.lastname: Tantillo
authors.forename: Jeffrey
authors.initials: J
authors.lastname: Aubé
mesh_terms: D000470:Alkaloids / Q000138:chemical synthesis; D001386:Azides / Q000737:chemistry*; D007769:Lactams / Q000138:chemical synthesis; D013141:Spiro Compounds / Q000138:chemical synthesis; D013237:Stereoisomerism
chemical_list: D000470:Alkaloids; D001386:Azides; D007769:Lactams; D013141:Spiro Compounds; C412665:pinnaic acid