Synthesis of dissymmetric indolocarbazole glycosides using the Mitsunobu reaction at the glycosylation step

Tetrahedron

Volumn 53, Issue 17, 1997, Pages 5937-5950

  Ohkubo, Mitsuru ^a   Nishimura, Teruyuki ^a   Jona, Hideki ^a   Honma, Teruki ^a   Ito, Satoru ^a   Morishima, Hajime ^a  

^a TAIHO PHARMACEUTICAL CO LTD   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

CARBAZOLE DERIVATIVE; GLYCOSIDE;

ARTICLE; DRUG SYNTHESIS; GLYCOSYLATION; IN VITRO STUDY; METHODOLOGY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; PRIORITY JOURNAL; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030936079     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(97)00286-X     Document Type: Article

References (27)

1. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsutiya, H.; Takahasi, Y.; Masuya, R. J. Antibiot. 1977, 30, 275. Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681. The absolute configuration of staurosporine has been disclosed: Futano, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y.; Iwai, Y.; Omura, S. Tetrahedron Lett. 1994, 35, 1251. Danishefsky reported the first total synthesis of staurosporine, see: Link, J.T.; Raghavan, S.; Danishefsky, S.J. J. Am. Chem. Soc. 1995, 117, 552.
2. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsutiya, H.; Takahasi, Y.; Masuya, R. J. Antibiot. 1977, 30, 275. Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681. The absolute configuration of staurosporine has been disclosed: Futano, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y.; Iwai, Y.; Omura, S. Tetrahedron Lett. 1994, 35, 1251. Danishefsky reported the first total synthesis of staurosporine, see: Link, J.T.; Raghavan, S.; Danishefsky, S.J. J. Am. Chem. Soc. 1995, 117, 552.
3. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsutiya, H.; Takahasi, Y.; Masuya, R. J. Antibiot. 1977, 30, 275. Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681. The absolute configuration of staurosporine has been disclosed: Futano, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y.; Iwai, Y.; Omura, S. Tetrahedron Lett. 1994, 35, 1251. Danishefsky reported the first total synthesis of staurosporine, see: Link, J.T.; Raghavan, S.; Danishefsky, S.J. J. Am. Chem. Soc. 1995, 117, 552.
4. Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsutiya, H.; Takahasi, Y.; Masuya, R. J. Antibiot. 1977, 30, 275. Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681. The absolute configuration of staurosporine has been disclosed: Futano, N.; Takayanagi, H.; Konda, Y.; Toda, Y.; Harigaya, Y.; Iwai, Y.; Omura, S. Tetrahedron Lett. 1994, 35, 1251. Danishefsky reported the first total synthesis of staurosporine, see: Link, J.T.; Raghavan, S.; Danishefsky, S.J. J. Am. Chem. Soc. 1995, 117, 552.
5. Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot. 1986, 39, 1059. Elliot, L.H.; Wilkinson, S.E.; Sedgwick, A.D.; Hill, C.H.; Lawton, G.; Davis, P.D.; Nixon, J.S. Biochem. Biophys. Res. Commun. 1990, 171, 148. Total synthesis of (+) and (-)-K252a was reported, see: Wood, J.L.; Stoltz, B.M.; Dietrich, H-J. J. Am. Chem. Soc. 1995, 117, 10413.
6. Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot. 1986, 39, 1059. Elliot, L.H.; Wilkinson, S.E.; Sedgwick, A.D.; Hill, C.H.; Lawton, G.; Davis, P.D.; Nixon, J.S. Biochem. Biophys. Res. Commun. 1990, 171, 148. Total synthesis of (+) and (-)-K252a was reported, see: Wood, J.L.; Stoltz, B.M.; Dietrich, H-J. J. Am. Chem. Soc. 1995, 117, 10413.
7. Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot. 1986, 39, 1059. Elliot, L.H.; Wilkinson, S.E.; Sedgwick, A.D.; Hill, C.H.; Lawton, G.; Davis, P.D.; Nixon, J.S. Biochem. Biophys. Res. Commun. 1990, 171, 148. Total synthesis of (+) and (-)-K252a was reported, see: Wood, J.L.; Stoltz, B.M.; Dietrich, H-J. J. Am. Chem. Soc. 1995, 117, 10413.
8. Nettleton, D.E.; Doyle, T.W.; Krishnan, B.; Matsumoto, G.K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011. Kaneko, T.; Wong, H.; Okamoto, K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. Bush, J.A.; Long, B.H.; Catino, J.J.; Bradner, W.T.; Tomita, K. J. Antibiot. 1987, 40, 668. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792.
9. Nettleton, D.E.; Doyle, T.W.; Krishnan, B.; Matsumoto, G.K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011. Kaneko, T.; Wong, H.; Okamoto, K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. Bush, J.A.; Long, B.H.; Catino, J.J.; Bradner, W.T.; Tomita, K. J. Antibiot. 1987, 40, 668. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792.
10. Nettleton, D.E.; Doyle, T.W.; Krishnan, B.; Matsumoto, G.K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011. Kaneko, T.; Wong, H.; Okamoto, K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. Bush, J.A.; Long, B.H.; Catino, J.J.; Bradner, W.T.; Tomita, K. J. Antibiot. 1987, 40, 668. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792.
11. Nettleton, D.E.; Doyle, T.W.; Krishnan, B.; Matsumoto, G.K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011. Kaneko, T.; Wong, H.; Okamoto, K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. Bush, J.A.; Long, B.H.; Catino, J.J.; Bradner, W.T.; Tomita, K. J. Antibiot. 1987, 40, 668. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792.
12. Nettleton, D.E.; Doyle, T.W.; Krishnan, B.; Matsumoto, G.K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4011. Kaneko, T.; Wong, H.; Okamoto, K.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. Bush, J.A.; Long, B.H.; Catino, J.J.; Bradner, W.T.; Tomita, K. J. Antibiot. 1987, 40, 668. Gallant, M.; Link, J.T.; Danishefsky, S.J. J. Org. Chem. 1993, 58, 343. Sancelme, M.; Fabre, S.; Prudhomme, M. J. Antibiot. 1994, 47, 792.
13. a) Arakawa, H.; Iguch, T.; Monta, M.; Yoshinari, T.; Kojiri, K.; Suda, H.; Okura, A.; Nishimura, S. Cancer Res. 1995, 55, 1316. Yoshinari, T.; Matsumoto, M.; Arakawa, H.; Okada, H.; Noguchi, K.; Suda, H.; Okura, A.; Nishimura, S. Cancer Res. 1995, 55, 1310.
14. a) Arakawa, H.; Iguch, T.; Monta, M.; Yoshinari, T.; Kojiri, K.; Suda, H.; Okura, A.; Nishimura, S. Cancer Res. 1995, 55, 1316. Yoshinari, T.; Matsumoto, M.; Arakawa, H.; Okada, H.; Noguchi, K.; Suda, H.; Okura, A.; Nishimura, S. Cancer Res. 1995, 55, 1310.
15. b) Ohkubo, M.; Kawamoto, K.; Ohno, T.; Nakano, M.; Morishima, H. Tetrahedron 1997, 585.
16. Ohkubo, M; Nishimura, T; Jona, H; Honma, T; Hajime, M. Tetrahedron 1996, 8099.
17. For a review, see: Mitsunobu, O. Synthesis 1981, 1-28. Huge, D.L. Organic Resactions; 1992, 335.
18. For a review, see: Mitsunobu, O. Synthesis 1981, 1-28. Huge, D.L. Organic Resactions; 1992, 335.
19. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
20. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
21. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
22. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
23. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
24. Szarek, W.A.; Depew, C.; Jarrell, H.C.; Jones, J.K.N. J. C. S. Chem. Comm. 1975, 648. Roush, W.R.; Lin, X-F. J. Org. Chem. 1991, 56, 5740. Delgado, A.; Clardy, J. J. Org. Chem. 1993, 58, 2862. Lubineau, A.; Meyer, E.; Place, P. Carbohydr. Res. 1992, 228, 191. Grochowski, E.; Stepowska, H. Stud. Org. Chem. (Amsterdam), 35 (Chem. Heterocycl. Compd.), 1988, 292
25. Tsunoda, T.; Yamamiya, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Ito, S. Chemistry Lett. 1994, 539.
26. Tsunoda, T.; Yamamiya, Y.; Ito, S. Tetrahedron Lett. 1993, 34, 1639. Tsunoda, T.; Otsuka, J.; Yamamiya, Y.; Ito, S. Chemistry Lett. 1994, 539.
27. We calculated the pKa values of 7 and 13 using MOPAC 6.0 (AMI). Yagil, D. Tetrahedron 1967, 2855.