Reaction of 4-acetoxy-2-azetidinone with tertiary carbanions: Preparation of 4-alkyl- and 4-alkylidene-2-azetidinones

Greengrass, C. W.; Hoople, David W. T.

doi:10.1016/s0040-4039(01)90264-3

Cited by 19 publications

(3 citation statements)

References 8 publications

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“…The 4-alkyliden-azetidin-2-ones represent a relatively new class of ␤-lactam compounds: few examples were studied in the 1980s (Greengrass and Hoople, 1981;Prasad et al, 1982), with no further development. These compounds have been recently obtained using an original and well established protocol starting from 4-acetoxy-azetidinones and diazoesters (Cainelli et al, 2003b).…”

Section: Resultsmentioning

confidence: 99%

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

Dell’Aica

Sartor

Galletti

et al. 2006

The Journal of Pharmacology and Experimental Therapeutics

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␤-Lactams, a well known class of antibiotics, have been investigated as inhibitors of the disruptive protease released by inflammatory cells, leukocyte elastase (LE). We have synthesized a new ␤-lactam with an N-linked galloyl moiety, the latter identified as strategic in conferring anti-LE properties to some flavonols. This N-galloyl-derivative ␤-lactam inhibits the LE activity with a K i of 0.7 M, whereas it exerts weak activity against cathepsin G and protease-3 (IC 50 Ͼ 100 M), and matrix metalloproteinase (MMP)-2 and MMP-9. Without affecting chemotactic response and viability of polymorphonuclear (PMN) leukocytes, the compound efficiently restrains their chemoinvasion (IC 50 of 1-2 M) blocking the LE-triggered activation of pro-MMP-9, instrumental to extravasation. Daily i.p. injection of compound enhances resolution in a pulmonary inflammation model, significantly reducing consequent fibrosis. These results indicate that the new ␤-lactam is a potent anti-inflammatory compound with therapeutic potential.

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Section: Resultsmentioning

confidence: 99%

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

Dell’Aica

Sartor

Galletti

et al. 2006

The Journal of Pharmacology and Experimental Therapeutics

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“…Our synthesis started with the commercially available 2-methoxycyclohexanone (Scheme ), which was (allyloxy)carbonylated using diallyl carbonate and sodium hydride in the presence of a catalytic amount of potassium hydride to produce the desired racemic β-ketoester 7 …”

Section: Resultsmentioning

confidence: 99%

A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

and

Rozema

1996

J. Am. Chem. Soc.

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A novel and practical total synthesis of a tricyclic β-lactam antibiotic, GV104326 (4-methoxytrinem or Sanfetrinem) has been achieved in nine steps and about 33% overall yield from a commercially available acetoxyazetidinone chiron. A key step in the highly diastereoselective synthesis is a protonation of a zinc enolate complex which circumvents the use of enantiomerically pure (S)-2-methoxycyclohexanone. A mechanistic rationale is presented and experimentally verified.

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“…For the primordial importance of trans/cis ‐ Hedione ® 6a / 6b in perfumery, see . A two‐step synthesis of DHH 1a was earlier performed by Rautenstrauch , and Vanhessche , via 1,4‐additions of either methyl(methylsulfinyl)acetate, or methyl(phenylsulfinyl)acetate, or methyl(phenylsulfonyl)acetate, or methyl nitroacetate, to 5a , followed in both first cases by thermal syn ‐elimination of either methyl‐, or phenyl‐sulfenic acid at 120 – 175 °C, respectively (60 – 66% overall yield). For a review on sulfoxide eliminations, see .…”

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confidence: 99%

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

Chapuis

Richard

2018

Helvetica Chimica Acta

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Dehydrohedione (DHH) 1a was obtained via a one pot, three step, domino procedure in 54% overall yield from 2a, by treatment with CuBr2, in MeOH at 65 °C. We demonstrated that the direct transformation of malonate derivative 2a into DHH 1a under CuX2 Kochi's conditions goes preferentially through the pathway involving intermediates 2b/2c and 7a, rather than 3a/3b or 8a/8b, essentially via α‐halogenation/dehydrohalogenation of the ketone moiety, both mediated by CuX2, while in‐situ decarbomethoxylation is promoted by the resulting CuX in refluxing MeOH.

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Reaction of 4-acetoxy-2-azetidinone with tertiary carbanions: Preparation of 4-alkyl- and 4-alkylidene-2-azetidinones

Cited by 19 publications

References 8 publications

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor

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Reaction of 4-acetoxy-2-azetidinone with tertiary carbanions: Preparation of 4-alkyl- and 4-alkylidene-2-azetidinones

Cited by 19 publications

References 8 publications

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

Inhibition of Leukocyte Elastase, Polymorphonuclear Chemoinvasion, and Inflammation-Triggered Pulmonary Fibrosis by a 4-Alkyliden-β-lactam with a Galloyl Moiety

A Highly Stereoselective and Practical Total Synthesis of the Tricyclic β-Lactam Antibiotic GV104326 (4-Methoxytrinem)

A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione® Precursor

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A One Pot Synthesis of Dehydrohedione (DHH) from a Hedione^® Precursor