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Tetrahedron Letters

Volumn 20, Issue 44, 1979, Pages 4287-4290

Synthetic studies on β-lactam antibiotics. part 11. Completely stereocontrolled synthesis of 7α-unsubstituted 1-oxacephems from penicillins

(10) Yoshioka, Mitsuru a Kikkawa, Ikuo a Tsuji, Teruji a Nishitani, Yasuhiro a Mori, Sachio a Okada, Kyo a Murakami, Masayuki a Matsubara, Fumihiko a Yamaguchi, Masaaki a Nagata, Wataru a

a SHIONOGI AND CO LTD (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

1 OXACEPHEM DERIVATIVE;

DRUG ANALYSIS; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE; THEORETICAL STUDY;

EID: 0018578683 PISSN: 00404039 EISSN: None Source Type: Journal
DOI: 10.1016/S0040-4039(01)86568-0 Document Type: Article

Times cited : (10)

References (24)

1
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- Part 10:
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- Narisada¹ Yoshida² Onoue³ Ohtani⁴ Okada⁵ Tsuji⁶ Kikkawa⁷ Haga⁸ Satoh⁹ Itani¹⁰ Nagata¹¹

2
- 84918347961
- The trivial name of 1-oxacephem(s) is used for 1-oxa-1-dethiacephalosporin(s); see ref 1.

3
- 84862780724
- Synthetic Studies on b-Lactam Antibiotics. Part 5. A Synthesis of 7b-Acylamino-3-methyl-1-oxadethia-3-cephem-4-carboxylic Acids
- (1977) HETEROCYCLES , vol.7 , pp. 839
- Narisada¹ Onoue² Nagata³

4
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- (1977) J. Med. Chem. , vol.20 , pp. 551
- Firestone¹ Fahey² Maciejewicz³ Patel⁴ Christensen⁵

5
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- (1974) J. Am. Chem. Soc. , vol.96 , pp. 7582
- Cama¹ Christensen²

6
- 0011243306
- Sulfur-free Penicillin Derivatives. VI. Synthesis of the 1-Oxacephem Ring System
- (1974) Canadian Journal of Chemistry , vol.52 , pp. 3996
- Wolfe¹ Ducep² Tin³ Lee⁴

7
- 0017913278
- (1978) Tetrahedron Lett. , pp. 409
- Kim¹ McGregor²

8
- 77954213769
- J. Elks, The Chemical Society, Burlington House, London
- (1977) Recent Advances in the Chemistry of β-lactam Antibiotics , pp. 204
- Brain¹ Branch² Eglington³ Nayler⁴ Osborne⁵ Pearson⁶ Smale⁷ Southgate⁸ Tolliday⁹

9
- 0007323506
- (1979) J. Am. Chem. Soc. , vol.101 , pp. 4403
- Uyeo¹ Kikkawa² Hamashima³ Ona⁴ Nishitani⁵ Okada⁶ Kubota⁷ Ishikura⁸ Ide⁹ Nakano¹⁰ Nagata¹¹

10
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- 3 in 6) in 48% yield.

11
- 0016411636
- The chemistry of penicillanic acids. Part III. A route to 1,2-secopenicillins
- (1975) Journal of the Chemical Society, Perkin Transactions 1 , vol.1 , pp. 562
- Brain¹ McMillan² Nayler³ Southgate⁴ Tolliday⁵

12
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- Japan. Patent 7,126,501
- (1971) Chem. Abstr. , vol.76 , pp. 3848n
- Murakami¹ Isaka² Kashiwagi³

13
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- Japan. Patent 7,126,501
- (1972) Chem. Abstr. , vol.76 , pp. 3848n
- Murakami¹ Isaka² Kashiwagi³

14
- 84918347959
- The stereochemistry at the asterisked carbon was not determined. Each of these compounds was obtained as a single epimer.

15
- 84918347958
- 6-AcOEt, silica gel).

16
- 84918347957
- 3 H), 7.38 and 7.42 (each s, 5 H, phenyl).

17
- 84918347956
- This Grignard process can be generally applied to conversion of esters to ketones: I. Kikkawa and T. Yorifugi, to be published.

18
- 84918347955
- 2H/t-BuOH also was effective, though yields of 3 were slightly lower.

19
- 84918347954
- 3, acetone).

20
- 0347357688
- (1964) J. Org. Chem. , vol.29 , pp. 3459
- King¹ Ostrum²

21
- 84918347953
- 3 H), 6.72 (d, 1 H, J = 8 Hz, amide H), 6.97 (s, 1 H, diphenylmethyl ester methine), ≈7.3 (m, 15 H, phenyl).

22
- 0010691554
- (1969) Bull. Soc. Chim. France , pp. 4169
- Gaudry¹ Marquet²

23
- 84918347952
- The reagents were added to the preceding hydrolysis mixture.

24
- 84918347951
- T. Yoshida, The Royal Society Discussion Meeting “Penicillin 50 years after Fleming”, London, May 1979, The Chemical Society, London: Abstr. p 10. A full account will appear soon in Philosophical Transactions of the Royal Society

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.