title: Asymmetric synthesis of the carbapenam core from serine.
abstract: The stereospecific synthesis of the functionalized carbapenam core 16 from the serine-derived trisubstituted pyrrolidine 9 is reported. The synthetic strategy relies on synthesizing an appropriately functionalized pyrrolidine, followed by an intramolecular azetidone formation utilizing a modified Mukiyama reagent. The efficient one-pot conversion of the benzenesulfonamide-protected pyrrolidine 9 to the Cbz-protected pyrrolidine 10 is also reported.
authors.affiliation: Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA. barry.hart.b@bayer.com
authors.forename: Barry P
authors.initials: BP
authors.lastname: Hart
authors.forename: Sharad K
authors.initials: SK
authors.lastname: Verma
authors.forename: Henry
authors.initials: H
authors.lastname: Rapoport
mesh_terms: D015780:Carbapenems / Q000138:chemical synthesis*; D007202:Indicators and Reagents; D015394:Molecular Structure; D019906:Nuclear Magnetic Resonance, Biomolecular; D011759:Pyrrolidines / Q000737:chemistry; D012694:Serine / Q000737:chemistry*; D013237:Stereoisomerism
chemical_list: D015780:Carbapenems; D007202:Indicators and Reagents; D011759:Pyrrolidines; D012694:Serine