Practical Synthesis of the Trisubstituted Naphthalene Carboxylic Acid from Neocarzinostatin Chromophore

Synlett

Volumn 1997, Issue 10, 1997, Pages 1187-1189

  Rucker, Mark ^a   Brückner, Reinhard ^a  

^a UNIVERSITY OF GÖTTINGEN   (Germany)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 1842639021     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1997-983     Document Type: Article

References (47)

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4. Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198. Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329. Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991. Saito, I. Toxicol. Lett. 1993, 67, 3-15.
5. Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198. Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329. Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991. Saito, I. Toxicol. Lett. 1993, 67, 3-15.
6. Goldberg; I. H. Acc. Chem. Res. 1991, 24, 191-198. Hirama, M. in Recent Progress in the Chemical Synthesis of Antibiotics and Related Microbial Products, Vol. 2 (G. Lukacs, Ed.), Springer, Berlin, 1993, 293-329. Hirama, M. J. Synth. Org. Chem. Jpn. 1994, 52, 980-991. Saito, I. Toxicol. Lett. 1993, 67, 3-15.
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11. Stereostructure of the sugar moiety of 1a: Edo, K.; Akiyama, Y.; Saito, K.; Mizugaki, M. J. Antibiot. 1986, 39, 1615-1619. Stereostructure of the aglycon of 1a: Myers, A. G.; Proteau, P. J.; Handel, T. M. J. Am. Chem. Soc. 1988, 110, 7212-7214.
12. Myers, A. G.; Harrington, P. M.; Kwon, B.-M. J. Am. Chem. Soc. 1992, 114, 1086-1087.
13. Myers, A. G.; Proteau, P. J. J. Am. Chem. Soc. 1989, 111, 1146-1147; Myers, A. G.; Cohen, S. B.; Kwon, B.-M. J. Am. Chem. Soc. 1994, 116, 1670-1682.
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15. Reviews: Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 93-124. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518. Suffert, J.; Bruckner, R. Lettre des Sciences Chimiques, février-avril 1996, 25-29.
16. Reviews: Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 93-124. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518. Suffert, J.; Bruckner, R. Lettre des Sciences Chimiques, février-avril 1996, 25-29.
17. Reviews: Lhermitte, H.; Grierson, D. Contemp. Org. Synth. 1996, 3, 93-124. Grissom, J. W.; Gunawardena, G. U.; Klingberg, D.; Huang, D. Tetrahedron 1996, 52, 6453-6518. Suffert, J.; Bruckner, R. Lettre des Sciences Chimiques, février-avril 1996, 25-29.
18. Myers, A. G.; Hammond, M.; Wu, Y.; Xiang, J.-N.; Harrington, P. M.; Kuo, E. Y. J. Am. Chem. Soc. 1996, 118, 10006-10007.
19. Eckhardt, M.; Brückner, R. Angew. Chem. 1996, 108, 1185-1188; Angew. Chem. Int. Ed. Engl. 1996, 35, 1093-1096. Eckhardt, M.; Brückner, R. Liebigs Ann. / Recueil 1997, 947-959.
20. Eckhardt, M.; Brückner, R. Angew. Chem. 1996, 108, 1185-1188; Angew. Chem. Int. Ed. Engl. 1996, 35, 1093-1096. Eckhardt, M.; Brückner, R. Liebigs Ann. / Recueil 1997, 947-959.
21. Eckhardt, M.; Brückner, R. Angew. Chem. 1996, 108, 1185-1188; Angew. Chem. Int. Ed. Engl. 1996, 35, 1093-1096. Eckhardt, M.; Brückner, R. Liebigs Ann. / Recueil 1997, 947-959.
22. Fern, F.; Brückner, R. Liebigs Ann. / Recueil 1997, 961-965.
23. Base-induced cycloaromatization of 1a: Hensens, O. D.; Helms, G. L.; Zink, D. L.; Chin, D.-H.; Kappen, L. S.; Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 11030-11031 (cf. also: Lamothe, M.; Fuchs, P. L. J. Am. Chem. Soc. 1993, 115, 4483-4496; Elbaum, D.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 1994, 4, 309-314). Light-induced cycloaromatization of 1a: Gomibuchi, T.; Hirama, M. J. Antibiot. 1995, 48, 738-740 (for the light-induced decomposition of 1a cf. Gomibuchi, T.; Fujiwara, K.; Nehira, T.; Hirama, M. Tetrahedron Lett. 1993, 34, 5753-5756).
24. Base-induced cycloaromatization of 1a: Hensens, O. D.; Helms, G. L.; Zink, D. L.; Chin, D.-H.; Kappen, L. S.; Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 11030-11031 (cf. also: Lamothe, M.; Fuchs, P. L. J. Am. Chem. Soc. 1993, 115, 4483-4496; Elbaum, D.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 1994, 4, 309-314). Light-induced cycloaromatization of 1a: Gomibuchi, T.; Hirama, M. J. Antibiot. 1995, 48, 738-740 (for the light-induced decomposition of 1a cf. Gomibuchi, T.; Fujiwara, K.; Nehira, T.; Hirama, M. Tetrahedron Lett. 1993, 34, 5753-5756).
25. Base-induced cycloaromatization of 1a: Hensens, O. D.; Helms, G. L.; Zink, D. L.; Chin, D.-H.; Kappen, L. S.; Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 11030-11031 (cf. also: Lamothe, M.; Fuchs, P. L. J. Am. Chem. Soc. 1993, 115, 4483-4496; Elbaum, D.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 1994, 4, 309-314). Light-induced cycloaromatization of 1a: Gomibuchi, T.; Hirama, M. J. Antibiot. 1995, 48, 738-740 (for the light-induced decomposition of 1a cf. Gomibuchi, T.; Fujiwara, K.; Nehira, T.; Hirama, M. Tetrahedron Lett. 1993, 34, 5753-5756).
26. Base-induced cycloaromatization of 1a: Hensens, O. D.; Helms, G. L.; Zink, D. L.; Chin, D.-H.; Kappen, L. S.; Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 11030-11031 (cf. also: Lamothe, M.; Fuchs, P. L. J. Am. Chem. Soc. 1993, 115, 4483-4496; Elbaum, D.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 1994, 4, 309-314). Light-induced cycloaromatization of 1a: Gomibuchi, T.; Hirama, M. J. Antibiot. 1995, 48, 738-740 (for the light-induced decomposition of 1a cf. Gomibuchi, T.; Fujiwara, K.; Nehira, T.; Hirama, M. Tetrahedron Lett. 1993, 34, 5753-5756).
27. Base-induced cycloaromatization of 1a: Hensens, O. D.; Helms, G. L.; Zink, D. L.; Chin, D.-H.; Kappen, L. S.; Goldberg, I. H. J. Am. Chem. Soc. 1993, 115, 11030-11031 (cf. also: Lamothe, M.; Fuchs, P. L. J. Am. Chem. Soc. 1993, 115, 4483-4496; Elbaum, D.; Schreiber, S. L. Bioorg. Med. Chem. Lett. 1994, 4, 309-314). Light-induced cycloaromatization of 1a: Gomibuchi, T.; Hirama, M. J. Antibiot. 1995, 48, 738-740 (for the light-induced decomposition of 1a cf. Gomibuchi, T.; Fujiwara, K.; Nehira, T.; Hirama, M. Tetrahedron Lett. 1993, 34, 5753-5756).
28. Takahashi, K.; Tanaka, T.; Suzuki, T.; Hirama, M. Tetrahedron 1994, 50, 1327-1340.
29. Hensens, O. D.; Giner, J.-L.; Goldberg, I. H. J. Am. Chem. Soc. 1989, 111, 3295-3299.
30. 5. The initiating 4 steps followed a procedure of Hauser, F. M.; Pogany, S. A. Synthesis 1980, 814-815.
31. Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1989, 30, 111-112. Compound 8 (Girard, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328) was initially subjected to 2 steps described by Rubottom, G. M.; Krueger, D. S., Tetrahedron Lett. 1977, 611-614.
32. Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1989, 30, 111-112. Compound 8 (Girard, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328) was initially subjected to 2 steps described by Rubottom, G. M.; Krueger, D. S., Tetrahedron Lett. 1977, 611-614.
33. Shishido, K.; Yamashita, A.; Hiroya, K.; Fukumoto, K.; Kametani, T. Tetrahedron Lett. 1989, 30, 111-112. Compound 8 (Girard, C.; Conia, J. M. Tetrahedron Lett. 1974, 3327-3328) was initially subjected to 2 steps described by Rubottom, G. M.; Krueger, D. S., Tetrahedron Lett. 1977, 611-614.
34. Myers, A. G.; Subramanian, V.; Hammond, M. Tetrahedron Lett. 1996, 37, 587-590.
35. 14.
36. Gruter, G.-J. M.; Akkerman, O. S.; Bickelhaupt, F. J. Org. Chem. 1994, 59, 4473-4481.
37. Procedure analogous to Edwards, J. D.; Cashaw, J. L. J. Am. Chem. Soc. 1956, 78, 3821-3824.
38. 3), IR spectra (film), and correct combustion analyses.
39. Procedure analogous to Tietze, L. F.; Eicher, T. Reaktionen und Synthesen, Georg Thieme Verlag, Stuttgart 1991, 2. Auflage, pp. 143-144.
40. Procedure analogous to Heck, R. F.; Ziegler, C. B. J. Org. Chem. 1978, 43, 2941-2946 and Voigt, K.; Lansky, A.; de Meijere, A. Liebigs Ann. 1996, 899-911.
41. Procedure analogous to Heck, R. F.; Ziegler, C. B. J. Org. Chem. 1978, 43, 2941-2946 and Voigt, K.; Lansky, A.; de Meijere, A. Liebigs Ann. 1996, 899-911.
42. trans = 16.2, 3-H).
43. Method: Youn, I. K.; Yon, G. H.; Pak, C. S. Tetrahedron Lett. 1986, 27, 2409-2410; Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287-5290.
44. Method: Youn, I. K.; Yon, G. H.; Pak, C. S. Tetrahedron Lett. 1986, 27, 2409-2410; Hudlicky, T.; Sinai-Zingde, G.; Natchus, M. G. Tetrahedron Lett. 1987, 28, 5287-5290.
45. m = 2.6, 3′-H, 5′-H).
46. m = 2.2 and 2.7, respectively, 6-H, 8-H), 13.31 (s, OH).
47. Method: Williams, D. R.; Lowder, P. D.;. Gu, Y.; Brooks, D. A. Tetrahedron Lett. 1997, 38, 331-334.