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

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

10 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

Bibliographical note

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

Keywords

Azetidinones
Carbapenems
Condensation
Enolates
Ozonolysis
Stereoselective

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

Access to Document

10.1016/j.tet.2003.11.048

Cite this

@article{9c6dcf8f8747456ba4bfe832b4564a15,

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",

month = jan,

day = "19",

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

language = "English",

volume = "60",

pages = "867--870",

journal = "Tetrahedron",

issn = "0040-4020",

publisher = "Elsevier Ltd",

number = "4",

}

TY - JOUR

T1 - A highly diastereoselective synthesis of a 1-β-methylcarbapenem intermediate using titanium enolate of 2′-hydroxypropiophenone

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

UR - http://www.scopus.com/inward/record.url?scp=0348230606&partnerID=8YFLogxK

UR - http://www.scopus.com/inward/citedby.url?scp=0348230606&partnerID=8YFLogxK

U2 - 10.1016/j.tet.2003.11.048

DO - 10.1016/j.tet.2003.11.048

M3 - Article

AN - SCOPUS:0348230606

SN - 0040-4020

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

Bibliographical note

Keywords

ASJC Scopus subject areas

Access to Document

Other files and links

Fingerprint

Cite this