Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate

Yoshio Ito, Yuko Kobayashi, Takeo Kawabata, Mitsuru Takase, Shiro Terashima

Research output: Contribution to journalArticle

106 Citations (Scopus)

Abstract

Two types of the carbapenem key intermediates (4 and 6) have been efficiently synthesized from inexpensive (S)-ethyl lactate (7). Thus, (S)-2-benzyloxypropanal readily obtainable from 7 was condensed with di-p-anisylmethylamine to give the chiral imine. The [2+2]-cycloaddition reaction of diketene with the imine underwent in a highly stereoselective manner, yielding the desired 3,4-trans-3-acetyl-β-lactam (13a) as a major product (diastereoselectivity 7∼10:1). This was elaborated to 4 and 6 in 9 and 6 steps, respectively.

Original languageEnglish
Pages (from-to)5767-5790
Number of pages24
JournalTetrahedron
Volume45
Issue number18
DOIs
Publication statusPublished - 1989
Externally publishedYes

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Carbapenems
Imines
Lactams
Cycloaddition
Cycloaddition Reaction
2-azetidinone
ethyl lactate
diketene

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

Cite this

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title = "Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate",
abstract = "Two types of the carbapenem key intermediates (4 and 6) have been efficiently synthesized from inexpensive (S)-ethyl lactate (7). Thus, (S)-2-benzyloxypropanal readily obtainable from 7 was condensed with di-p-anisylmethylamine to give the chiral imine. The [2+2]-cycloaddition reaction of diketene with the imine underwent in a highly stereoselective manner, yielding the desired 3,4-trans-3-acetyl-β-lactam (13a) as a major product (diastereoselectivity 7∼10:1). This was elaborated to 4 and 6 in 9 and 6 steps, respectively.",
author = "Yoshio Ito and Yuko Kobayashi and Takeo Kawabata and Mitsuru Takase and Shiro Terashima",
year = "1989",
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issn = "0040-4020",
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TY - JOUR

T1 - Novel syntheses of the carbapenem key intermediates, (3R,4R)-4-acetoxy-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-2-azetidinone and (3S,4R)-3-[(R)-1-(t-butyldimethylsilyloxy)ethyl]-4-carboxymethyl-2-azetidinone, from (S)-ethyl lactate

AU - Ito, Yoshio

AU - Kobayashi, Yuko

AU - Kawabata, Takeo

AU - Takase, Mitsuru

AU - Terashima, Shiro

PY - 1989

Y1 - 1989

N2 - Two types of the carbapenem key intermediates (4 and 6) have been efficiently synthesized from inexpensive (S)-ethyl lactate (7). Thus, (S)-2-benzyloxypropanal readily obtainable from 7 was condensed with di-p-anisylmethylamine to give the chiral imine. The [2+2]-cycloaddition reaction of diketene with the imine underwent in a highly stereoselective manner, yielding the desired 3,4-trans-3-acetyl-β-lactam (13a) as a major product (diastereoselectivity 7∼10:1). This was elaborated to 4 and 6 in 9 and 6 steps, respectively.

AB - Two types of the carbapenem key intermediates (4 and 6) have been efficiently synthesized from inexpensive (S)-ethyl lactate (7). Thus, (S)-2-benzyloxypropanal readily obtainable from 7 was condensed with di-p-anisylmethylamine to give the chiral imine. The [2+2]-cycloaddition reaction of diketene with the imine underwent in a highly stereoselective manner, yielding the desired 3,4-trans-3-acetyl-β-lactam (13a) as a major product (diastereoselectivity 7∼10:1). This was elaborated to 4 and 6 in 9 and 6 steps, respectively.

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U2 - 10.1016/S0040-4020(01)89105-5

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JF - Tetrahedron

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