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Tetrahedron Letters

Volumn 26, Issue 44, 1985, Pages 5363-5366

Cyclobutanone analogs of β-lactam antibiotics: sythesis of n-acetyldeazathienamycin

(2) Cocuzza, A J a Boswell, G A a

a DUPONT COMPANY (United States)

Author keywords

[No Author keywords available]

Indexed keywords

THIENAMYCIN DERIVATIVE;

DRUG ANALYSIS; DRUG IDENTIFICATION; DRUG SYNTHESIS; INFRARED SPECTROMETRY; N ACETYLDEAZATHIENAMYCIN; NONHUMAN; NUCLEAR MAGNETIC RESONANCE; PRELIMINARY COMMUNICATION; PRIORITY JOURNAL; THEORETICAL STUDY;

EID: 0022352057 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(00)98208-X Document Type: Article

Times cited : (19)

References (22)

1
- 0018343188
- (1978) J. Antibiot. , vol.32 , pp. 1
- Kahan¹ Kahan² Goegelman³ Currie⁴ Jackson⁵ Stapley⁶ Miller⁷ Miller⁸ Hendlin⁹ Mochales¹⁰ Hernandez¹¹ Woodruff¹² Birnbaum¹³

2
- 0019864162
- (1981) Nature , vol.289 , pp. 590
- Imada¹ Kitano² Kintaka³ Muroi⁴ Asai⁵

3
- 0016372484
- For a description of the reactivity of the β-lactam ring in penicillins and cephalosporins see:
- (1974) J. Med. Chem. , vol.17 , pp. 523
- Indelicato¹ Norvilas² Pfeiffer³ Wheeler⁴ Wilham⁵

4
- 0019514597
- (1981) Tetrahedron Lett. , pp. 1871
- Gordon¹ Pluscec² Ondetti³

5
- 37049091785
- Carbocyclic analogues of penicllin
- (1982) Journal of the Chemical Society, Chemical Communications , pp. 90
- Meth-Cohn¹ Reason² Roberts³

6
- 37049110679
- Synthesis of 7?-phenylacetamido-6-oxo-2-oxabicyclo[3.2.0]heptane-4?-carboxylic acid, a cyclobutanone analogue of a ?-lactam antibiotic
- (1983) Journal of the Chemical Society, Chemical Communications , pp. 1279
- Lowe¹ Swain²

7
- 37049142272
- Novel rearrangement of the adduct of 6,6-dimethylfulvene and dichloroketen
- For examples of cycloadducts of ketenes with fulvenes see
- (1970) Journal of the Chemical Society D: Chemical Communications , pp. 89
- Asao¹ Takahisa² Tervo³ Kitahava⁴

8
- 37049140008
- (1971) J. Chem. Soc. (c) , pp. 3645
- Harmon¹ Barta² Gupta³ Slomp⁴

9
- 84918399688
- This structure was confirmed by x-ray crystallographic analysis.

10
- 84918399687
- The free carboxylic acid corresponding to 1 has been synthesized by similar chemistry involving cycloaddition of dichloroketene to 6,6-bis(methylthio)fulvene (ref. 4).

11
- 84918399686
- −1.

12
- 0018871826
- These conditions for double bond isomerization were first reported in a thienamycin total synthesis:
- (1980) J. Org. Chem. , vol.45 , pp. 1142
- Schmitt¹ Johnston² Christensen³

13
- 84918399685
- 3 SnLi, −78→25°, 30 min; ii, MeLi/PhCOCl, THF, −78°, 10 min; iii, 4N HCl, HOAc, 25°, 10 min.

14
- 84918399684
- For a description of rates of β-lactam hydrolysis, see ref. 3.

15
- 84918399683
- This structure was confirmed by x-ray crystallographic analysis of a derivative (sulfone dimethylketal).

16
- 0000923722
- (1980) Tetrahedron Lett. , pp. 4607
- Yamamoto¹ Maruyama²

17
- 0000244225
- Aldol diastereoselection zirconium enolates. Product-selective, enolate structure independent condensations.
- (1980) Tetrahedron Letters , pp. 3975
- Evans¹ McGee²

18
- 84918399682
- −1.

19
- 84918399681
- The acetyl derivative of deazathienamycin was prepared for ease in isolation and identification. N-Acetylthienamycin is a naturally occurring substance with similar antibacterial activity to thienamycin (see ref. 1).

20
- 84918399680
- −1.

21
- 84918399679
- Typical antibacterial MIC's vs. S. aureus were 25–50 μg/ml. The anti-betalactamase activity of these compounds was determined by demonstration of synergism with penicillin G against betalactamase producing strains of S. aureus.

22
- 0021945484
- (1985) Tetrahedron Lett. , pp. 1791
- Lange¹ Savard² Viswanatha³ Dmitrienko⁴

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