Asymmetric synthesis of the carbapenam core from serine.
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.
Hart
Barry P
BP
Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA. barry.hart.b@bayer.com
Verma
Sharad K
SK
Rapoport
Henry
H
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
D015780:Carbapenems; D007202:Indicators and Reagents; D011759:Pyrrolidines; D012694:Serine