A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation

Woo Baeg Choi; Hywyn R.O. Churchill; Joseph E. Lynch; Andrew S. Thompson; Guy R. Humphrey; R. P. Volante; Paul J. Reider; Ichiro Shinkai

doi:10.1016/0040-4039(94)85197-2

A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation

Woo Baeg Choi, Hywyn R.O. Churchill, Joseph E. Lynch, Andrew S. Thompson, Guy R. Humphrey, R. P. Volante, Paul J. Reider, Ichiro Shinkai

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23 Scopus citations

Abstract

(3S,4S)-3[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone 7a was prepared from (3R,4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxy)ethyl]-2-azetidinone 3 via a sequence involving coupling with 2,2,5-trimethyl-1,3-dioxan-4,6-dione 4, N-silylation, solvolysis of the methylmeldrum's acid moiety and a stereoselective acid catalyzed decarboxylation.

Original language	English (US)
Pages (from-to)	2275-2278
Number of pages	4
Journal	Tetrahedron Letters
Volume	35
Issue number	15
DOIs	https://doi.org/10.1016/0040-4039(94)85197-2
State	Published - Apr 11 1994
Externally published	Yes

All Science Journal Classification (ASJC) codes

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/0040-4039(94)85197-2

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title = "A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation",

abstract = "(3S,4S)-3[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone 7a was prepared from (3R,4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxy)ethyl]-2-azetidinone 3 via a sequence involving coupling with 2,2,5-trimethyl-1,3-dioxan-4,6-dione 4, N-silylation, solvolysis of the methylmeldrum's acid moiety and a stereoselective acid catalyzed decarboxylation.",

author = "Choi, \{Woo Baeg\} and Churchill, \{Hywyn R.O.\} and Lynch, \{Joseph E.\} and Thompson, \{Andrew S.\} and Humphrey, \{Guy R.\} and Volante, \{R. P.\} and Reider, \{Paul J.\} and Ichiro Shinkai",

year = "1994",

month = apr,

day = "11",

doi = "10.1016/0040-4039(94)85197-2",

language = "English (US)",

volume = "35",

pages = "2275--2278",

journal = "Tetrahedron Letters",

issn = "0040-4039",

publisher = "Elsevier Ltd",

number = "15",

}

TY - JOUR

T1 - A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation

AU - Choi, Woo Baeg

AU - Churchill, Hywyn R.O.

AU - Lynch, Joseph E.

AU - Thompson, Andrew S.

AU - Humphrey, Guy R.

AU - Volante, R. P.

AU - Reider, Paul J.

AU - Shinkai, Ichiro

PY - 1994/4/11

Y1 - 1994/4/11

N2 - (3S,4S)-3[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone 7a was prepared from (3R,4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxy)ethyl]-2-azetidinone 3 via a sequence involving coupling with 2,2,5-trimethyl-1,3-dioxan-4,6-dione 4, N-silylation, solvolysis of the methylmeldrum's acid moiety and a stereoselective acid catalyzed decarboxylation.

AB - (3S,4S)-3[(R)-1-(t-Butyldimethylsilyloxy)ethyl]-4-[(R)-1-carboxyethyl]-2-azetidinone 7a was prepared from (3R,4R)-4-acetoxy-3-[(R)-1-t-butyldimethylsilyloxy)ethyl]-2-azetidinone 3 via a sequence involving coupling with 2,2,5-trimethyl-1,3-dioxan-4,6-dione 4, N-silylation, solvolysis of the methylmeldrum's acid moiety and a stereoselective acid catalyzed decarboxylation.

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U2 - 10.1016/0040-4039(94)85197-2

DO - 10.1016/0040-4039(94)85197-2

M3 - Article

AN - SCOPUS:0028280840

SN - 0040-4039

VL - 35

SP - 2275

EP - 2278

JO - Tetrahedron Letters

JF - Tetrahedron Letters

IS - 15

ER -

A stereoselective synthesis of a key 1β-methylcarbapenem intermediate via a diastereoselective decarboxylation

Abstract

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