Synthesis of the staurosporine aglycone (K-252c) lactam regioisomer

Tetrahedron Letters

Volumn 38, Issue 6, 1997, Pages 915-918

  Hudkins, Robert L ^a   Diebold, James L ^a  

^a CEPHALON INC   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

STAUROSPORINE DERIVATIVE;

ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; IN VITRO STUDY; INFRARED SPECTROPHOTOMETRY; MASS SPECTROMETRY; NUCLEAR MAGNETIC RESONANCE SPECTROSCOPY; REACTION ANALYSIS;

EID: 0031562076     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(96)02512-9     Document Type: Article

References (23)

1. 1. (a) Omura, S.; Iwai, Y.; Hirano, A.; Nakagawa, A.; Awaya, J.; Tsuchiya, H.; Takahashi, Y.; Masuma, R. J. Antibiot. 1977, 30, 275;
2. (b) Sezaki, M.; Sasaki, T.; Nakazawa, T.; Takeda, U.; Iwata, M.; Watanabe, T.; Koyama, M.; Kai, F.; Shomura, T.; Kojima, M. J. Antibiot. 1985, 38, 143;
3. (c) Kase, H.; Iwahashi, K.; Matsuda, Y. J. Antibiot 1986, 39, 1059;
4. (d) Nakanishi, S.; Matsuda, Y.; Iwahashi, K.; Kase, H. J. Antibiot. 1986, 39, 1066;
5. (e) Yasuzawa, T.; Iida, T.; Yoshida, M.; Hirayama, N.; Takahashi, M.; Shirahata, K.; Sano, H. J. Antibiot. 1986, 39, 1072.
6. 2. (a) Davis, P.D.; Hill, C.H.; Lawton,G.; Nixon, J.S.; Wilkinson, S.E.; Hurst, S.A.; Keech, E.; Turner, S.E. J. Med. Chem. 1992, 35, 177.
7. (b) Vice, S.F.; Bishop, W.R.; McCombie, S.W.; Dao, H.; Frank, E.; Ganguly, A.K. BioMed. Chem. Lett. 1994, 4, 1333.
8. (c) McCombie, S.W.; Bishop, R.W.; Carr, D.; Dobek, E.; Kirkup, P.; Kirshmeier, P.; Lin, S.,; Petrin, J.; Rosinski, K.; Shankar, B.B.; Wilson, O. BioMed. Chem. Lett. 1993, 3, 1537.
9. (d) Fabre S.; Prudhomme, M.; Rapp, M. BioMed. Chem. 1993, 3, 193.
10. 3. (a) Bruning, J.; Hache, T.; Winterfildt, E. Synthesis 1994, 25.
11. (b) Moody, C.J.; Rahimtola, K.F.; Porter, B.; Ross, B.C. J. Org. Chem. 1992, 57, 2105.
12. (c) Harris, W.; Hill, C.H.; Keech, E.; Malsher, P. Tetrahedron Lett. 1993, 34, 8361.
13. (d) Xie, G.; Lown, J.W. Tetrahedron Lett. 1994, 35, 5555.
14. 4. (a) Reimers, W.A. In Indoles Pt 1; Houlihan, W.J. Ed.; Wiley: New York, 1972;
15. (b) Colonna, M; Monti, A. Gazz. Chim. Ital. 1962, 92, 1401;
16. (c) Appleton, J.E.; Dack, K.N.; Green, A.D.; Steel, J. Tetrahedron Lett. 1993, 34, 1529;
17. (d) Barry, J.F.; Wallace, T.W.; Walshe, N.D.A. Tetrahedron 1995, 47, 12797.
18. 5. (a) Kaneko, T.; Wong, H.; Okamoto, K. T.; Clardy, J. Tetrahedron Lett. 1985, 26, 4015.
19. (b) Somei, M.; Kodama, A. Heterocycles 1992, 34, 1285.
20. (c) Wood, J. L.; Stoltz, B. M.; Dietrich, H-J. J. Am. Chem. Soc. 1995, 117, 10413.
21. 6. Hudkins, R.L.; Diebold, J.L.; Marsh, F.D. J. Org. Chem. 1995, 60, 6218.
22. 2O, (C, H, N ± 0.4%).
23. 8. An authentic sample of the natural K-252c (3) was kindly provided by Dr. C. Murakata, Tokyo Researsh Labs, Kyowa Hakko Kogyo Co., Ltd.