Synthesis of an anti-methicillin-resistant Staphylococcus aureus (MRSA) carbapenem via stannatrane-mediated Stille coupling.
[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.
Jensen
M S
MS
Department of Process Research, Merck Research Laboratories, Rahway, New Jersey 07065, USA. mark_jensen@merck.com
Yang
C
C
Hsiao
Y
Y
Rivera
N
N
Wells
K M
KM
Chung
J Y
JY
Yasuda
N
N
Hughes
D L
DL
Reider
P J
PJ
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*
C408868:1-stanna-5-azabicyclo(3.3.3)undecane; D001643:Bridged Bicyclo Compounds; D015780:Carbapenems; D009947:Organotin Compounds