A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone

You Sang Lee; Won Keun Choung; Kyoung Hoon Kim; Tae Won Kang; Deok Chan Ha

doi:10.1016/j.tet.2003.11.048

A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone

You Sang Lee, Won Keun Choung, Kyoung Hoon Kim, Tae Won Kang, Deok Chan Ha

College of Science

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

4 Citations (Scopus)

Abstract

A key 1-β-methylcarbapenem intermediate is synthesized from a highly diastereoselective condensation between the titanium enolate of 2′-hydroxypropiophenone with 4-acetoxy-β-lactam followed by ozonolysis of the resulting ketone to the carboxylic acid.

Original language	English
Pages (from-to)	867-870
Number of pages	4
Journal	Tetrahedron
Volume	60
Issue number	4
DOIs	https://doi.org/10.1016/j.tet.2003.11.048
Publication status	Published - 2004 Jan 19

Keywords

Azetidinones
Carbapenems
Condensation
Enolates
Ozonolysis
Stereoselective

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2003.11.048

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title = "A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone",

abstract = "A key 1-β-methylcarbapenem intermediate is synthesized from a highly diastereoselective condensation between the titanium enolate of 2′-hydroxypropiophenone with 4-acetoxy-β-lactam followed by ozonolysis of the resulting ketone to the carboxylic acid.",

keywords = "Azetidinones, Carbapenems, Condensation, Enolates, Ozonolysis, Stereoselective",

author = "Lee, {You Sang} and Choung, {Won Keun} and Kim, {Kyoung Hoon} and Kang, {Tae Won} and Ha, {Deok Chan}",

note = "Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST and ChongKunDang Pharm.",

year = "2004",

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doi = "10.1016/j.tet.2003.11.048",

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AU - Lee, You Sang

AU - Choung, Won Keun

AU - Kim, Kyoung Hoon

AU - Kang, Tae Won

AU - Ha, Deok Chan

N1 - Funding Information: This work was financially supported by the Center for Molecular Design and Synthesis (CMDS) at KAIST and ChongKunDang Pharm.

PY - 2004/1/19

Y1 - 2004/1/19

N2 - A key 1-β-methylcarbapenem intermediate is synthesized from a highly diastereoselective condensation between the titanium enolate of 2′-hydroxypropiophenone with 4-acetoxy-β-lactam followed by ozonolysis of the resulting ketone to the carboxylic acid.

AB - A key 1-β-methylcarbapenem intermediate is synthesized from a highly diastereoselective condensation between the titanium enolate of 2′-hydroxypropiophenone with 4-acetoxy-β-lactam followed by ozonolysis of the resulting ketone to the carboxylic acid.

KW - Azetidinones

KW - Carbapenems

KW - Condensation

KW - Enolates

KW - Ozonolysis

KW - Stereoselective

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DO - 10.1016/j.tet.2003.11.048

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VL - 60

SP - 867

EP - 870

JO - Tetrahedron

JF - Tetrahedron

IS - 4

ER -

A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone

Abstract

Keywords

ASJC Scopus subject areas

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