SCOPUS 정보 검색 플랫폼

Organic Letters

Volumn 2, Issue 8, 2000, Pages 1153-1154

An expeditious synthesis of (±)-desepoxy-4,5-didehydromethylenomycin A methyl ester

(2) Balczewski, Piotr a Mikolajczyk, Marian a

a CENTRE OF MOLECULAR AND MACROMOLECULAR STUDIES (Poland)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001015809 PISSN: 15237060 EISSN: None Source Type: Journal
DOI: 10.1021/ol005742b Document Type: Article

Times cited : (16)

References (33)

1
- 0042039826
- Lucakcs, G., Ed.; Springer-Verlag: Berlin
- See, for example: Mathew, J. In Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbiological Products; Lucakcs, G., Ed.; Springer-Verlag: Berlin, 1993; Vol. 2, pp 435-474.
- (1993) Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbiological Products , vol.2 , pp. 435-474
- Mathew, J.¹

2
- 0016188242
- Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M. J. Antibiot. 1974, 27, 386-392. Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot. 1974, 27, 393-399. Haneishi, T.; Terahara, A.; Hamano, K.; Arai, M. J. Antibiot. 1974, 27, 400-407.
- (1974) J. Antibiot. , vol.27 , pp. 386-392
- Haneishi, T.¹ Kitahara, N.² Takiguchi, Y.³ Arai, M.⁴

3
- 0016258164
- Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M. J. Antibiot. 1974, 27, 386-392. Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot. 1974, 27, 393-399. Haneishi, T.; Terahara, A.; Hamano, K.; Arai, M. J. Antibiot. 1974, 27, 400-407.
- (1974) J. Antibiot. , vol.27 , pp. 393-399
- Haneishi, T.¹ Terahara, A.² Arai, M.³ Hata, T.⁴ Tamura, C.⁵

4
- 0016192934
- Haneishi, T.; Kitahara, N.; Takiguchi, Y.; Arai, M. J. Antibiot. 1974, 27, 386-392. Haneishi, T.; Terahara, A.; Arai, M.; Hata, T.; Tamura, C. J. Antibiot. 1974, 27, 393-399. Haneishi, T.; Terahara, A.; Hamano, K.; Arai, M. J. Antibiot. 1974, 27, 400-407.
- (1974) J. Antibiot. , vol.27 , pp. 400-407
- Haneishi, T.¹ Terahara, A.² Hamano, K.³ Arai, M.⁴

5
- 0342303124
- For a recent summary, see: Mikolajczyk, M.; Mikina, M.; Zurawinski, R. Pure Appl. Chem. 1999, 71, 473-480.
- (1999) Pure Appl. Chem. , vol.71 , pp. 473-480
- Mikolajczyk, M.¹ Mikina, M.² Zurawinski, R.³

6
- 0019957980
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1982) Tetrahedron Lett. , vol.23 , pp. 2237-2240
- Mikolajczyk, M.¹ Grzejszczak, S.² Lyzwa, P.³

7
- 0021210705
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1984) Synthesis , pp. 691-694
- Mikolajczyk, M.¹ Balczewski, P.²

8
- 0019957980
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1987) Synthesis , pp. 659-661

9
- 0026034618
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1991) J. Org. Chem. , vol.56 , pp. 1217-1223
- Mikolajczyk, M.¹ Zatorski, A.²

10
- 84954236446
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1991) Synlett , pp. 575-576
- Mikolajczyk, M.¹ Zurawinski, R.²

11
- 0002256416
- Mikolajczyk, M.; Grzejszczak, S.; Lyzwa, P. Tetrahedron Lett. 1982, 23, 2237-2240. Mikolajczyk, M.; Balczewski, P. Synthesis 1984, 691-694; 1987, 659-661. Mikolajczyk, M.; Zatorski, A. J. Org. Chem. 1991, 56, 1217-1223. Mikolajczyk, M.; Zurawinski, R. Synlett 1991, 575-576. Balczewski, P. Heteroatom. Chem. 1997, 8, 67-69.
- (1997) Heteroatom. Chem. , vol.8 , pp. 67-69
- Balczewski, P.¹

12
- 0030990828
- Mikolajczyk, M.; Zurawinski, R.; Kielbasinski, P.; Wieczorek, M. W.; Blaszczyk, J. Synthesis 1997, 356-365.
- (1997) Synthesis , pp. 356-365
- Mikolajczyk, M.¹ Zurawinski, R.² Kielbasinski, P.³ Wieczorek, M.W.⁴ Blaszczyk, J.⁵

13
- 0003186687
- Mikolajczyk, M.; Mikina, M.; Wieczorek, M. W.; Blaszczyk, J. Angew. Chem. 1996, 108, 1645-1647; Angew. Chem., Int. Ed. Engl. 1996, 35, 1560-1562.
- (1996) J. Angew. Chem. , vol.108 , pp. 1645-1647
- Mikolajczyk, M.¹ Mikina, M.² Wieczorek, M.W.³ Blaszczyk⁴

14
- 0029759656
- Mikolajczyk, M.; Mikina, M.; Wieczorek, M. W.; Blaszczyk, J. Angew. Chem. 1996, 108, 1645-1647; Angew. Chem., Int. Ed. Engl. 1996, 35, 1560-1562.
- (1996) Angew. Chem., Int. Ed. Engl. , vol.35 , pp. 1560-1562

15
- 0031767572
- Mikolajczyk, M.; Zurawinski, R. J. Org. Chem. 1998, 63, 8894-8897. Mikolajczyk, M.; Mikina, M.; Jankowiak, A.; Mphahlele, M. J. Submitted.
- (1998) J. Org. Chem. , vol.63 , pp. 8894-8897
- Mikolajczyk, M.¹ Zurawinski, R.²

16
- 0031767572
- Submitted
- Mikolajczyk, M.; Zurawinski, R. J. Org. Chem. 1998, 63, 8894-8897. Mikolajczyk, M.; Mikina, M.; Jankowiak, A.; Mphahlele, M. J. Submitted.
- Mikolajczyk, M.¹ Mikina, M.² Jankowiak, A.³ Mphahlele, M.J.⁴

17
- 0043251497
- Submitted
- Mikolajczyk, M.; Mikina, M.; Jankowiak, A. Submitted.
- Mikolajczyk, M.¹ Mikina, M.² Jankowiak, A.³

18
- 0043251495
- The methyl ester 2b is more stable than the corresponding free acid 2a. It is also expected to be more biologically active than 2a as was found in the case of methylenomycin A 1 methyl ester which showed stronger antibacterial and antifungal activity than methylenomycin A itself
- The methyl ester 2b is more stable than the corresponding free acid 2a. It is also expected to be more biologically active than 2a as was found in the case of methylenomycin A 1 methyl ester which showed stronger antibacterial and antifungal activity than methylenomycin A itself.

19
- 0018386866
- For previous syntheses of (±)-2b, see: Sakai, K.; Amemiya, S.; Inoue, K.; Kojima, K. Tetrahedron Lett. 1979, 25, 2365-2368. Boschelli, D.; Scarborough, R. M. Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 27, 19-22. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett. 1989, 30, 3857-3860. Hong, F.-T.; Lee, K.-S.; Liao, Ch.-Ch. Tetrahedron Lett. 1992, 33, 2155-2158. Tius, M. A.; Kwok, Ch.-K.; Gu, X.; Zhao, Ch. Synth. Commun. 1994, 24, 871-885.
- (1979) Tetrahedron Lett. , vol.25 , pp. 2365-2368
- Sakai, K.¹ Amemiya, S.² Inoue, K.³ Kojima, K.⁴

20
- 0019368266
- For previous syntheses of (±)-2b, see: Sakai, K.; Amemiya, S.; Inoue, K.; Kojima, K. Tetrahedron Lett. 1979, 25, 2365-2368. Boschelli, D.; Scarborough, R. M. Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 27, 19-22. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett. 1989, 30, 3857-3860. Hong, F.-T.; Lee, K.-S.; Liao, Ch.-Ch. Tetrahedron Lett. 1992, 33, 2155-2158. Tius, M. A.; Kwok, Ch.-K.; Gu, X.; Zhao, Ch. Synth. Commun. 1994, 24, 871-885.
- (1981) Tetrahedron Lett. , vol.27 , pp. 19-22
- Boschelli, D.¹ Scarborough R.M., Jr.² Smith A.B. III³

21
- 0024359306
- For previous syntheses of (±)-2b, see: Sakai, K.; Amemiya, S.; Inoue, K.; Kojima, K. Tetrahedron Lett. 1979, 25, 2365-2368. Boschelli, D.; Scarborough, R. M. Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 27, 19-22. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett. 1989, 30, 3857-3860. Hong, F.-T.; Lee, K.-S.; Liao, Ch.-Ch. Tetrahedron Lett. 1992, 33, 2155-2158. Tius, M. A.; Kwok, Ch.-K.; Gu, X.; Zhao, Ch. Synth. Commun. 1994, 24, 871-885.
- (1989) Tetrahedron Lett. , vol.30 , pp. 3857-3860
- Mahidol, C.¹ Thebtaranonth, C.² Thebtaranonth, Y.³ Yenjai, C.⁴

22
- 0026506973
- For previous syntheses of (±)-2b, see: Sakai, K.; Amemiya, S.; Inoue, K.; Kojima, K. Tetrahedron Lett. 1979, 25, 2365-2368. Boschelli, D.; Scarborough, R. M. Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 27, 19-22. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett. 1989, 30, 3857-3860. Hong, F.-T.; Lee, K.-S.; Liao, Ch.-Ch. Tetrahedron Lett. 1992, 33, 2155-2158. Tius, M. A.; Kwok, Ch.-K.; Gu, X.; Zhao, Ch. Synth. Commun. 1994, 24, 871-885.
- (1992) Tetrahedron Lett. , vol.33 , pp. 2155-2158
- Hong, F.-T.¹ Lee, K.-S.² Liao, Ch.-Ch.³

23
- 0028208455
- For previous syntheses of (±)-2b, see: Sakai, K.; Amemiya, S.; Inoue, K.; Kojima, K. Tetrahedron Lett. 1979, 25, 2365-2368. Boschelli, D.; Scarborough, R. M. Jr.; Smith, A. B., III. Tetrahedron Lett. 1981, 27, 19-22. Mahidol, C.; Thebtaranonth, C.; Thebtaranonth, Y.; Yenjai, C. Tetrahedron Lett. 1989, 30, 3857-3860. Hong, F.-T.; Lee, K.-S.; Liao, Ch.-Ch. Tetrahedron Lett. 1992, 33, 2155-2158. Tius, M. A.; Kwok, Ch.-K.; Gu, X.; Zhao, Ch. Synth. Commun. 1994, 24, 871-885.
- (1994) Synth. Commun. , vol.24 , pp. 871-885
- Tius, M.A.¹ Kwok, Ch.-K.² Gu, X.³ Zhao, Ch.⁴

24
- 0043251496
- Tiglic acid chloride was obtained from commercially available trans-2-methyl-2-butenoic acid (tiglic acid)
- Tiglic acid chloride was obtained from commercially available trans-2-methyl-2-butenoic acid (tiglic acid).

25
- 0041748631
- Attempted phenylselenylation of the sodium salt of 4 with phenylselenenyl bromide as an alternative way for introduction of the olefinic bond failed
- Attempted phenylselenylation of the sodium salt of 4 with phenylselenenyl bromide as an alternative way for introduction of the olefinic bond failed.

26
- 0001070304
- H,P-cis ∼ 20 Hz): Lehnert, W. Tetrahedron 1974, 30, 301-305. Reetz, M. T.; Peter, R.; von Itzstein, M.; Chem. Ber. 1987, 120, 121-122. Nickson, T. E. J. Org. Chem. 1988, 53, 3870. Midura, W. H.; Mikolajczyk, M.; Tetrahedron Lett. 1995, 36, 2871-2874.
- (1974) Tetrahedron , vol.30 , pp. 301-305
- Lehnert, W.¹

27
- 84984188413
- H,P-cis ∼ 20 Hz): Lehnert, W. Tetrahedron 1974, 30, 301-305. Reetz, M. T.; Peter, R.; von Itzstein, M.; Chem. Ber. 1987, 120, 121-122. Nickson, T. E. J. Org. Chem. 1988, 53, 3870. Midura, W. H.; Mikolajczyk, M.; Tetrahedron Lett. 1995, 36, 2871-2874.
- (1987) Chem. Ber. , vol.120 , pp. 121-122
- Reetz, M.T.¹ Peter, R.² Von Itzstein, M.³

28
- 0003178740
- H,P-cis ∼ 20 Hz): Lehnert, W. Tetrahedron 1974, 30, 301-305. Reetz, M. T.; Peter, R.; von Itzstein, M.; Chem. Ber. 1987, 120, 121-122. Nickson, T. E. J. Org. Chem. 1988, 53, 3870. Midura, W. H.; Mikolajczyk, M.; Tetrahedron Lett. 1995, 36, 2871-2874.
- (1988) J. Org. Chem. , vol.53 , pp. 3870
- Nickson, T.E.¹

29
- 0028957356
- H,P-cis ∼ 20 Hz): Lehnert, W. Tetrahedron 1974, 30, 301-305. Reetz, M. T.; Peter, R.; von Itzstein, M.; Chem. Ber. 1987, 120, 121-122. Nickson, T. E. J. Org. Chem. 1988, 53, 3870. Midura, W. H.; Mikolajczyk, M.; Tetrahedron Lett. 1995, 36, 2871-2874.
- (1995) Tetrahedron Lett. , vol.36 , pp. 2871-2874
- Midura, W.H.¹ Mikolajczyk, M.²

30
- 0001057224
- Minami, T.; Nakayama, M.; Fujimoto, K.; Matsuo, S. Phosphorus, Sulfur. Silicon Relat. Elem. 1993, 75, 135-138. Motoyoshija, J.; Mizuno, K.; Tsuda, T.; Hayashi, S. Synlett 1993, 237-238.
- (1993) Phosphorus, Sulfur. Silicon Relat. Elem. , vol.75 , pp. 135-138
- Minami, T.¹ Nakayama, M.² Fujimoto, K.³ Matsuo, S.⁴

31
- 0001766978
- Minami, T.; Nakayama, M.; Fujimoto, K.; Matsuo, S. Phosphorus, Sulfur. Silicon Relat. Elem. 1993, 75, 135-138. Motoyoshija, J.; Mizuno, K.; Tsuda, T.; Hayashi, S. Synlett 1993, 237-238.
- (1993) Synlett , pp. 237-238
- Motoyoshija, J.¹ Mizuno, K.² Tsuda, T.³ Hayashi, S.⁴

32
- 0003594801
- Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, New York, Basel, Cambridge
- Krohn, K. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, New York, Basel, Cambridge, 1991; pp 137-144. Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1-158.
- (1991) Organic Synthesis Highlights , pp. 137-144
- Krohn, K.¹

33
- 0001992172
- Krohn, K. In Organic Synthesis Highlights; Mulzer, J., Altenbach, H.-J., Braun, M., Krohn, K.; Reissig, H.-U. Eds.; VCH: Weinheim, New York, Basel, Cambridge, 1991; pp 137-144. Habermas, K. L.; Denmark, S. E.; Jones, T. K. Org. React. 1994, 45, 1-158.
- (1994) Org. React. , vol.45 , pp. 1-158
- Habermas, K.L.¹ Denmark, S.E.² Jones, T.K.³

* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.