Stereochemical course of the [4+2] cycloaddition of 1-methoxybuta-1,3-diene to N-glyoxyloyl-(2R)-bornane-10,2-sultam. The formal synthesis of compactin and mevinolin

Tetrahedron Asymmetry

Volumn 7, Issue 5, 1996, Pages 1391-1404

  Bauer, Tomasz ^a,b   Chapuis, Christian ^b,c   Jezewski, Artur ^b   Kozak, Janusz ^b   Jurczak, Janusz ^a,b  

^a UNIVERSITY OF WARSAW   (Poland)

^b INSTITUTE OF ORGANIC CHEMISTRY   (Poland)

^c Email:   (Switzerland)

Author keywords

[No Author keywords available]

Indexed keywords

COMPACTIN; MEVINOLIN;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; PRIORITY JOURNAL; REACTION ANALYSIS; X RAY ANALYSIS;

EID: 0029980787     PISSN: 09574166     EISSN: None     Source Type: Journal    
DOI: 10.1016/0957-4166(96)00156-5     Document Type: Article

References (49)

1. Konował, A.; Jurczak, J.; Zamojski, A. Tetrahedron 1976, 32, 2957.
2. Zamojski, A; Banaszek, A.; Grynkiewicz, G. Adv. Carbohydr. Chem. Biochem. 1982, 40, 1.
3. Zamojski, A.; Grynkiewicz, G. In The Total Synthesis of Natural Products; ApSimon, J. W.; Ed.; J. Wiley: Chichester, 1984, Vol. 6, pp. 141-235.
4. Chmielewski, M.; Jurczak, J.; Zamojski, A. Tetrahedron, 1978, 34, 2977.
5. Chmielewski, M.; Jurczak, J. J. Org. Chem. 1981, 46, 2230.
6. Jurczak, J.; Zamojski, A. Tetrahedron 1972, 28, 1505.
7. Jurczak, J. Polish J. Chem. 1979, 53, 2539.
8. Oppolzer, W.; Chapuis, C.; Bernardinelli, G. Helv. Chim. Acta 1984, 67, 1397.
9. Bauer, T.; Chapuis, C.; Kozak, J; Jurczak, J. Helv. Chim. Acta 1989, 72, 482.
10. Bauer, T.; Jeżewski, A.; Chapuis, C.; Jurczak, J. Tetrahedron: Asymmetry, preceding paper.
11. Jurczak, J.; Bauer, T.; Gołȩbiowski, A. Bull. Pol. Acad. Chem. 1985, 33, 397.
12. Bednarski, M.; Danishefsky, S. J. Am. Chem. Soc. 1983, 105, 3716.
13. Jurczak, J; Gołȩbiowski, A.; Bauer T. Synthesis 1985, 928.
14. Gero, S. D.; Guthrie, R. D. J. Chem. Soc. (C) 1967, 1761.
15. Oppolzer, W.; Poli, G.; Starkeman, C.; Bernardinelli, G. Tetrahedron Lett. 1988, 29, 3559.
16. Curran, D. P.; Kim, B. H.; Daugherty, J.; Heffner, T. A. Tetrahedron Lett. 1988, 29, 3555.
17. Chapuis, C.; de Saint Laumer, J-Y. presented at the IX ESOC, Warsaw, Poland, June 1995.
18. Chapuis, C.; de Saint Laumer, J-Y.Marty, M. Helv. Chim. Acta, in preparation.
19. Kim, K. S.; Kim, B. H.; Park, W. M.; Cho, S. J.; Mhin, B. J. J. Am. Chem. Soc. 1993, 115, 7472.
20. Jurczak, J.; Tkacz, M. J. Org. Chem. 1979, 44, 3347.
21. Chapuis, C. Ph.D. Thesis; Universite de Geneve; 1984; No. 2144.
22. Gouverneur, V., Ghosez, L. Tetrahedron: Asymmetry 1990, 1, 363.
23. Gouverneur, V.; Dive, G.; Ghosez, L. Tetrahedron: Asymmetry 1991, 2, 1173.
24. Chapuis, C.; Rzepecki, P.; Bauer, T.; Jurczak, J. Helv. Chim. Acta 1995, 78, 145.
25. Kim, B. H.; Curran, D. P. Tetrahedron 1993, 49, 293.
26. Oppolzer, W.; Barras, G. P. Helv. Chim. Acta 1987, 70, 1666.
27. For a recent example of supposedly electronic dependence, see: Iseki, K; Oishi, S.; Komayashi, Y. Chem. Lett. 1994, 1135. For recent examples of electronic p-facial stereoselection in the Diels-Alder reactions, see: references cited in ref. 24.
28. Klopman, G. J. Am. Chem. Soc. 1968, 90, 223.
29. Salem, L. J. Am. Chem. Soc. 1968, 90, 543, 553.
30. Oppolzer, W. presented at the First Anglo-Norman Organic Chemistry Colloquium, Rouen, France, May 1991.
31. Pindur, U.; Lutz, G.; Fischer, G.; Massa, W.; Schroder, L.; Schollmeyer, D. Tetrahedron 1993, 49, 2863.
32. Epimerization of the anomeric center of the cycloadducts 4 and 6 is not excluded under the reaction conditions and may explain the apparent exo-selectivity of the attack.
33. Oppolzer, W.; Rodriguez, J.; Blagg, J.; Bernardinelli, G. Helv. Chim. Acta 1989, 72, 123.
34. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2939.
35. Montagna, A. E.; Hirsch, D. H. US Patent 1959, 2905772; Chem. Abstr. 1960, 54, 2168.
36. Bauer, T.; Kozak, J.; Chapuis, C.; Jurczak, J. J. Chem. Soc., Chem. Commun. 1990, 1178.
37. Endo, A. J. Med. Chem. 1985, 28, 401.
38. Rosen, T.; Heathcock, C. H. Tetrahedron 1986, 42, 4909.
39. Stokker, G. E.; Hoffmann, W. F.; Alberts, A. W.; Cragoe, E. J.; Deana, A. A.; Gilfilan, J. L.; Huff, J. W.; Norello, F. C.; Prugh, J. D.; Smith, R. L.; Willard, A. K. J. Med. Chem. 1985, 28, 347.
40. Roth, B. D.; Roark, W. H. Tetrahedron. Lett. 1988, 29, 1255.
41. Johnson, W. S.; Kelson, A. B.; Elliott, J. D. Tetrahedron Lett. 1989, 29, 3757.
42. Takano, S.; Shimazaki, Y.; Sekiguchi, Y.; Ogasawara, K. Synthesis 1989, 539.
43. Bauer, T.; Jeżewski, A.; Jurczak, J. Tetrahedron: Asymmetry, following paper.
44. Mieczkowski, J.; Jurczak, J.; Chmielewski, M.; Zamojski, A. Carbohydrate Res. 1977, 56, 180.
45. Chmielewski, M.; Jurczak, J.; Maciejewski, S. Carbohydrate Res. 1987, 165, 111.
46. Flack, H.D.; Acta Cryst. 1983, C39, 876.
47. Sheldrick, G.M.; 1985 Program for the Solution of Crystal Structures, University of Göttingen, Germany.
48. Sheldrick, G.M.; 1993, Program for the Refinement of Crystal Structures, University of Göttingen, Germany.
49. Bauer, T.; Krajewski, J.W.; Kemme, A. J. Chem. Cryst., submitted.