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Asymmetric synthesis of the carbapenam core from serine
Barry P Hart1, Sharad K Verma, Henry Rapoport
1Department of Chemistry, University of California, Berkeley, Berkeley, California 94720, USA. barry.hart.b@bayer.com
The Journal of Organic Chemistry
|January 8, 2003
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.