Stereocontrolled total synthesis of (+)-K252a [3]

Journal of the American Chemical Society

Volumn 121, Issue 27, 1999, Pages 6501-6502

  Kobayashi, Yoshihisa ^a   Fujimoto, Teppei ^a   Fukuyama, Tohru ^a  

^a JAPAN SCIENCE AND TECHNOLOGY AGENCY   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

K 252A;

DIASTEREOISOMER; DRUG STRUCTURE; DRUG SYNTHESIS; LETTER; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0033554020     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja990909l     Document Type: Letter

References (36)

1. (+)-K252a was isolated independently by two Japanese groups, (a) Sezaki, M.; Sasaki, T.; Nakazawa, T.; Takeda, U.; Iwata, M.; Watanabe, T.; Koyama, M.; Kai, F.; Shomura, T.; Kojima, M. J. Antibiot. 1985, 38, 1439. (b) Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot. 1986, 39, 1059.
2. (+)-K252a was isolated independently by two Japanese groups, (a) Sezaki, M.; Sasaki, T.; Nakazawa, T.; Takeda, U.; Iwata, M.; Watanabe, T.; Koyama, M.; Kai, F.; Shomura, T.; Kojima, M. J. Antibiot. 1985, 38, 1439. (b) Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot. 1986, 39, 1059.
3. For structure elucidation of (+)-K252a, see: (a) Nakanishi, S.; Matsuda, Y.; Iwahashi, K.; Kase, H. J. Antibiot. 1986, 39, 1066. (b) Yasuzawa, T.; Iida, T.; Yoshida, M.; Hirayama, M.; Takahashi, M.; Shirahata, K.; Sano, H. J. Antibiot. 1986, 39, 1072.
4. For structure elucidation of (+)-K252a, see: (a) Nakanishi, S.; Matsuda, Y.; Iwahashi, K.; Kase, H. J. Antibiot. 1986, 39, 1066. (b) Yasuzawa, T.; Iida, T.; Yoshida, M.; Hirayama, M.; Takahashi, M.; Shirahata, K.; Sano, H. J. Antibiot. 1986, 39, 1072.
5. For isolation and structure elucidation of (+)-staurosporine, see: (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275. (b) Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. J. Chem. Soc., Chem. Commun. 1978, 800. (c) Furasaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681.
6. For isolation and structure elucidation of (+)-staurosporine, see: (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275. (b) Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. J. Chem. Soc., Chem. Commun. 1978, 800. (c) Furasaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681.
7. For isolation and structure elucidation of (+)-staurosporine, see: (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275. (b) Furusaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. J. Chem. Soc., Chem. Commun. 1978, 800. (c) Furasaki, A.; Hashiba, N.; Matsumoto, T.; Hirano, A.; Iwai, Y.; Omura, S. Bull. Chem. Soc. Jpn. 1982, 55, 3681.
8. (a) Magnus, P. D.; Sear, N. L. Tetrahedron 1984, 40, 2797.
9. (b) Bruning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
10. (c) Kobayashi, Y.; Fukuyama, T. J. Heterocycl. Chem. 1998, 35, 1043.
11. (a) Wood, J. L.; Stoltz, B. M.; Dietrich, H.-J. J. Am. Chem. Soc. 1995, 117, 10413.
12. (b) Wood, J, L.; Stoltz, B. M.; Dietrich, H.-J.; Pflum, D. A.; Petsch, D. T. J. Am. Chem. Soc. 1997, 119, 9641.
13. (a) Link, J. L.; Raghavan, S.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 552.
14. (b) Link, J. L.; Raghavan, S.; Gallant, M.; Danishefsky, S. J.; Chou, T. C.; Ballas, L. M. J. Am. Chem. Soc. 1996, 118, 2825.
15. Zhang, P.; Liu, R.; Cook, J. M. Tetrahedron Lett. 1995, 36, 3103.
16. Girgis, N. S.; Cottam, H. B.; Robins, R. K. J. Heterocycl. Chem. 1988, 25, 361.
17. Hoffer, M. Chem. Ber. 1960, 93, 2777.
18. Oikawa, Y.; Yonemitsu, O. J. Org. Chem. 1977, 42, 1213.
19. Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469.
20. Lactam 13 exists as a 1:1 mixture of atropisomers.
21. For an example of a nonoxidative photochemical synthesis of phenanthrenes, see: Cava, M. P.; Mitchell, M. J.; Havlicek, S. C.; Lindert, A.; Spangler, R. J. J. Org. Chem. 1970, 35, 175.
22. A 500-W halogen lamp can be used in laboratories.
23. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
24. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
25. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
26. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
27. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
28. For syntheses of indolocarbazoles by means of less effective, oxidative photocyclization, see: (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015. (b) Weinreb, S. M.; Garigipati, R. S.; Gainor, J. A. Heterocycles 1984, 21, 309. (c) Harris, W.; Hill, C. H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361. (d) Xie, G.; Lown, J. W. Tetrahedron Lett. 1994, 35, 5555. (e) Sarstedt, B.; Winterfeldt, E. Heterocycles 1983, 20, 469. (f) Brüning, J.; Hache, T.; Winterfeldt, E. Synthesis 1994, 25.
29. Classon, B.; Liu, Z.; Samuelsson, B. J. Org. Chem. 1988, 53, 6126.
30. For the selenoxide elimination step, triethylamine and DHP were added to prevent the undesired oxidative addtion of phenylselenous acid to the reactive enol ether.
31. 2, NBS, NIS, bromine, iodine, ICl, bromopyridinium pyridine tetrafluoroborate, and acid catalysts such as CSA, PPTS, and Amberlyst were examined. Under these conditions, 21 suffered extensive decomposition.
32. 3, and the heightened HOMO level of the enol ether due to the proximate indolyl anion, enabling a concerted reaction to take place.
33. Kuivila, H. G.; Menapace, L. W. J. Org. Chem. 1963, 28, 2165.
34. Use of more basic triethylamine as a base gave, after acetylation, a 3:1 mixture of 26a and 26b. (22) The unprotected cyanohydrin was prone to lose hydrogen cyanide to give ketone 25.
35. Becke, F.; Fleig, H.; Pässler, P. Liebigs Ann. Chem. 1971, 749, 198.
36. We are indebted to Dr. C. Murakata of Kyowa Hakko Kogyo for a generous gift of natural (+)-K252a.