Asymmetric synthesis of the carbapenam core from serine

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

doi:10.1021/jo026499s

Asymmetric synthesis of the carbapenam core from serine

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

Research output: Contribution to journal › Article › peer-review

8 Scopus citations

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 language	English (US)
Pages (from-to)	187-190
Number of pages	4
Journal	Journal of Organic Chemistry
Volume	68
Issue number	1
DOIs	https://doi.org/10.1021/jo026499s
State	Published - Jan 10 2003
Externally published	Yes

ASJC Scopus subject areas

Organic Chemistry

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title = "Asymmetric synthesis of the carbapenam core from serine",

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.",

author = "Hart, {Barry P.} and Verma, {Sharad K.} and Henry Rapoport",

year = "2003",

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AU - Verma, Sharad K.

AU - Rapoport, Henry

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N2 - 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.

AB - 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.

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Asymmetric synthesis of the carbapenam core from serine

Abstract

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