title: Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.
abstract: [formula: see text] A short synthesis of carbapenem 1 is described. They key step involves the cross-coupling of an enol triflate with an amino-substituted sp3 carbon. This cross-couping, which allows the introduction of the complete side chain in one step, utilizes a stannatrane as the heteroalkyl transfer reagent.
authors.affiliation: Department of Process Research, Merck Research Laboratories, Rahway, New Jersey 07065, USA. mark_jensen@merck.com
authors.forename: M S
authors.initials: MS
authors.lastname: Jensen
authors.forename: C
authors.initials: C
authors.lastname: Yang
authors.forename: Y
authors.initials: Y
authors.lastname: Hsiao
authors.forename: N
authors.initials: N
authors.lastname: Rivera
authors.forename: K M
authors.initials: KM
authors.lastname: Wells
authors.forename: J Y
authors.initials: JY
authors.lastname: Chung
authors.forename: N
authors.initials: N
authors.lastname: Yasuda
authors.forename: D L
authors.initials: DL
authors.lastname: Hughes
authors.forename: P J
authors.initials: PJ
authors.lastname: Reider
mesh_terms: D001643:Bridged Bicyclo Compounds / Q000737:chemistry*; D015780:Carbapenems / Q000138:chemical synthesis*; D016106:Methicillin Resistance; D009947:Organotin Compounds / Q000737:chemistry*; D013211:Staphylococcus aureus / Q000187:drug effects*
chemical_list: C408868:1-stanna-5-azabicyclo(3.3.3)undecane; D001643:Bridged Bicyclo Compounds; D015780:Carbapenems; D009947:Organotin Compounds