A new synthesis of staurosporinone

Tetrahedron

Volumn 54, Issue 24, 1998, Pages 6909-6918

  Beccalli, Egle M ^a   Gelmi, Maria Luisa ^a   Marchesini, Alessandro ^a  

^a UNIVERSITY OF MILAN   (Italy)

Author keywords

Alkaloids; Coupling reactions; Electrocyclic reactions; Indoles

Indexed keywords

3 CYANO 3 (1H INDOL 3 YL) 2 OXOPROPIONIC ACID ETHYL ESTER; CARBAZOLE DERIVATIVE; STAUROSPORINE; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; PRIORITY JOURNAL; REACTION ANALYSIS; SYNTHESIS;

EID: 0032507907     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(98)00372-X     Document Type: Article

References (41)

1. [1] Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya Y, Tsuchiya H. J. Antibiot. 1977; 30: 275. Funato N, Takayanagi H, Konda Y, Toda Y, Harigaya Y, Iwai Y, Omura S, Tetrahedron Lett. 1994; 35: 1251.
2. [1] Omura S, Iwai Y, Hirano A, Nakagawa A, Awaya Y, Tsuchiya H. J. Antibiot. 1977; 30: 275. Funato N, Takayanagi H, Konda Y, Toda Y, Harigaya Y, Iwai Y, Omura S, Tetrahedron Lett. 1994; 35: 1251.
3. [2] Kase H, Iwahashi K, Matsuda Y. J. Antibiot. 1986; 39: 1059.
4. [3] Nettleton D E, Doyle T W, Krishnan B. Matsumoto G K, Clardy J. Tetrahedron Lett. 1985; 26: 4011. Pearce C J, Doyle T W, Forenza S, Lam K S, Schroeder D R. J. Nat. Prod. 1988; 51: 937.
5. [3] Nettleton D E, Doyle T W, Krishnan B. Matsumoto G K, Clardy J. Tetrahedron Lett. 1985; 26: 4011. Pearce C J, Doyle T W, Forenza S, Lam K S, Schroeder D R. J. Nat. Prod. 1988; 51: 937.
6. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
7. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
8. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
9. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
10. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
11. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
12. [4] Kase H, Iwahashi K, Nakanishi S, Matsuda Y, Yamada K, Takahashi M, Murakata C, Sato A, Kaneko M. Biochem Biophys. Res. Commun. 1987; 142: 436 Tamaoki T. Methods in Enzimology 1991; 201: 340. Nishizuka Y. ibid. 1983; 99: 288, Nishizuka Y. Nature 1988; 334: 661. Tamaoki T, Nomoto H, Takahashi I, Kato Y, Morimoto M, Tomita F. Biochem. Biophys. Res. Commun. 1986; 135: 397. Fujita-Yamaguchi Y, Kathuria S. ibid. 1988; 157: 955. Lam K S, Schroeder D R, Veitch J M, Maison J A, Forenza S. J. Antibiot. 1991; 44: 934.
13. [5] Knusel B, Hefti F. J. Neurochem. 1992; 59: 1987
14. [6] Nakanishi S, Matsuda Y, Iwahashi K, Kase H. J. Antibiot. 1986; 39: 1066. Yasurawa T, Lida T, Yoshida M, Hirayama N, Takahashi M, Shirabata K, Sano H. J. Antibiot. 1986; 39: 1072, Fröde R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich R. Tetrahedron Lett. 1994; 35: 1689. Horton P A, Longley R E, McConnell O J, Ballas L M. Experientia 1994; 50: 843. Faulkner D J. Natural Products Reports 1996; 13: 115.
15. [6] Nakanishi S, Matsuda Y, Iwahashi K, Kase H. J. Antibiot. 1986; 39: 1066. Yasurawa T, Lida T, Yoshida M, Hirayama N, Takahashi M, Shirabata K, Sano H. J. Antibiot. 1986; 39: 1072, Fröde R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich R. Tetrahedron Lett. 1994; 35: 1689. Horton P A, Longley R E, McConnell O J, Ballas L M. Experientia 1994; 50: 843. Faulkner D J. Natural Products Reports 1996; 13: 115.
16. [6] Nakanishi S, Matsuda Y, Iwahashi K, Kase H. J. Antibiot. 1986; 39: 1066. Yasurawa T, Lida T, Yoshida M, Hirayama N, Takahashi M, Shirabata K, Sano H. J. Antibiot. 1986; 39: 1072, Fröde R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich R. Tetrahedron Lett. 1994; 35: 1689. Horton P A, Longley R E, McConnell O J, Ballas L M. Experientia 1994; 50: 843. Faulkner D J. Natural Products Reports 1996; 13: 115.
17. [6] Nakanishi S, Matsuda Y, Iwahashi K, Kase H. J. Antibiot. 1986; 39: 1066. Yasurawa T, Lida T, Yoshida M, Hirayama N, Takahashi M, Shirabata K, Sano H. J. Antibiot. 1986; 39: 1072, Fröde R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich R. Tetrahedron Lett. 1994; 35: 1689. Horton P A, Longley R E, McConnell O J, Ballas L M. Experientia 1994; 50: 843. Faulkner D J. Natural Products Reports 1996; 13: 115.
18. [6] Nakanishi S, Matsuda Y, Iwahashi K, Kase H. J. Antibiot. 1986; 39: 1066. Yasurawa T, Lida T, Yoshida M, Hirayama N, Takahashi M, Shirabata K, Sano H. J. Antibiot. 1986; 39: 1072, Fröde R, Hinze C, Josten I, Schmidt B, Steffan B, Steglich R. Tetrahedron Lett. 1994; 35: 1689. Horton P A, Longley R E, McConnell O J, Ballas L M. Experientia 1994; 50: 843. Faulkner D J. Natural Products Reports 1996; 13: 115.
19. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
20. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
21. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
22. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
23. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
24. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
25. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
26. [7] Kasai M, et al. Chem. Abstr. 1996; 124: 56566, Murakata C, et al. Chem Abstr. 1996; 124: 87461. Lewis M E. et al. Chem. Abstr. 1996; 124: 202711. 1996; 125: 86967. Thiergardt R, et al. Chem. Abstr. 1997; 126: 212285 Fredenhagen A, et al. Chem. Abstr. 1997; 126: 212286. Wood J L, et al. Chem. Abstr. 1997; 126: 212287. Heath Jr W F, et al. Chem Abstr. 1997; 127: 17847.
27. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
28. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
29. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
30. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
31. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
32. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
33. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
34. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
35. [8] Sarstedt B, Winterfeldt E. Heterocycles 1983; 20: 469. Hughes I, Nolan W P, Raphael R A. J. Chem. Soc. Perkin Trans I 1990: 2475. Moody C J, Rahimtoola K F. J. Chem. Soc. Chem. Commun. 1990: 1677. Moody C J, Rahimtoola K F, Porter B, Ross B C. J. Org. Chem. 1992; 57: 2105. Harris W, Hill C, Keech E, Malsher P. Tetrahedron Lett. 1993; 34: 8361. Xie G, Lown J W. Tetrahedron Lett. 1994; 35: 5555. Wood J L, Stoltz B M, Dietrich H-J. J. Am. Chem. Soc. 1995; 117; 10413. Faul M H, Sullivan K A, Winneroski L. Synthesis 1995: 1511. Wood J L, Stoltz B M, Dietrich H-J, Pflum D A, Petsch D T. J. Am. Chem. Soc. 1997; 119: 9641.
36. [9] Rozhkov V S, Smushkevich Yu I, Kozik T A, Suvorov N N. Khim. Geterotsikl. Soedin. 1974; 11: 1502.
37. [10] Achab S. Tetrahedron Lett. 1996: 37: 5503.
38. [11] Liebeskind L S, Fengl R W. J. Org. Chem. 1990; 55: 5359. Farina V. Pure & Appl. Chem. 1996; 68 73.
39. [11] Liebeskind L S, Fengl R W. J. Org. Chem. 1990; 55: 5359. Farina V. Pure & Appl. Chem. 1996; 68 73.
40. [12] Satoh T, Suzuki S, Suzuki Y, Miyaji Y, Imai Z. Tetrahedron Lett. 1969: 4555, Heinzman S W, Ganem B. J. Am. Chem. Soc. 1982; 104: 6801.
41. [12] Satoh T, Suzuki S, Suzuki Y, Miyaji Y, Imai Z. Tetrahedron Lett. 1969: 4555, Heinzman S W, Ganem B. J. Am. Chem. Soc. 1982; 104: 6801.