Asymmetric synthesis of the carbapenam core from serine

Barry P. Hart, Sharad K. Verma, Henry Rapoport

Research output: Contribution to journalArticlepeer-review

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.

Original languageEnglish (US)
Pages (from-to)187-190
Number of pages4
JournalJournal of Organic Chemistry
Volume68
Issue number1
DOIs
StatePublished - Jan 10 2003
Externally publishedYes

ASJC Scopus subject areas

  • Organic Chemistry

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