Stereocontrolled total synthesis of (-)-eudistomin C

Journal of the American Chemical Society

Volumn 127, Issue 43, 2005, Pages 15038-15039

  Yamashita, Tohru ^a   Kawai, Nobutaka ^a,b   Tokuyama, Hidetoshi ^a   Fukuyama, Tohru ^a  

^a UNIVERSITY OF TOKYO   (Japan)

^b ASTELLAS PHARMA INC   (Japan)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; ALKALOID; EUDISTOMIN C; OXATHIAZEPINE DERIVATIVE; THIAZEPINE DERIVATIVE; TRYPTOLINE; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DIASTEREOISOMER; DRUG SYNTHESIS; PICTET SPENGLER REACTION; STEREOCHEMISTRY;

ANIMALS; ANTINEOPLASTIC AGENTS; ANTIVIRAL AGENTS; CARBOLINES; INDICATORS AND REAGENTS; MODELS, CHEMICAL; STEREOISOMERISM;

EID: 27544508842     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja055832h     Document Type: Article

References (31)

1. (a) Rinehart, K. L., Jr.; Kobayashi, J.; Harbour, G. C.; Hughes, R. G., Jr.; Mizsak, S. A.; Scahill, T. A. J. Am. Chem. Soc. 1984, 106, 1524.
2. (b) Kobayashi, J.; Harbour, G. C.; Gilmore, J.; Rinehart, K. L., Jr. J. Am. Chem. Soc. 1984, 106, 1526.
3. (c) Rinehart, K. L., Jr.; Kobayashi, J.; Harbour, G. C.; Gilmore, J.; Mascal, M.; Holt, T. G.; Shield, L. S.; Lafargue, F. J. Am. Chem. Soc. 1987, 109, 3378.
4. (d) Kobayashi, J.; Nakamura, H.; Ohizumi, Y. Tetrahedron Lett. 1986, 27, 1191.
5. (a) Lake, R. J.; Brennan, M. M.; Blunt, J. W.; Munro, M. H. G. Tetrahedron Lett. 1988, 29, 2255.
6. (b) Lake, R. J.; McCombs, J. D.; Blunt, J. W.; Munro, M. H. G.; Robinson, W. T. Tetrahedron Lett. 1988, 29, 4971.
7. (c) Lake, R. J.; Blunt, J. W.; Munro, M. H. Aust. J. Chem. 1989, 42, 1201.
8. (a) Nakagawa, M.; Liu, J.-J.; Hino, T. J. Am. Chem. Soc. 1989, 111, 2721.
9. (b) Nakagawa, M.; Liu, J.-J.; Hino, T.; Tsuruoka, A.; Harada, N.; Ariga, M.; Asada, Y. J. Chem. Soc., Perkin Trans. 1 2000, 3477.
10. Liu, J.-J.; Hino, T.; Tsuruoka, A.; Harada, N.; Nakagawa, M. J. Chem. Soc., Perkin Trans. 1 2000, 3487.
11. (a) Hermkens, P. H. H.; van Maarseveen, J. H.; Kruse, C. G.; Scheeren, H. W. Tetrahedron Lett. 1989, 30, 5009.
12. (b) Hermkens, P. H. H.; van Maarseveen, J. H.; Berens, H. W.; Smits, J. M. M.; Kruse, C. G.; Scheeren, H. W. J. Org. Chem. 1990, 55, 2200.
13. (c) Hermkens, P. H. H.; van Maarseveen, J. H.; Ottenheijm, H. C. J.; Kruse, C. G.; Scheeren, H. W. J. Org. Chem. 1990, 55, 3998.
14. (d) van Maarseveen, J. H.; Hermkens, P. H. H.; Clercq, E. D.; Balzarini, J.; Scheeren, H. W.; Kruse, C. G. J. Med. Chem. 1992, 35, 3223.
15. (e) van Maarseveen, J. H.; Scheeren, H. W.; Kruse, C. G. Tetrahedron 1993, 49, 2325.
16. (a) Han, S. Y.; Lakshmikantham, M. V.; Cava, M. P. Heterocycles 1985, 23, 1671.
17. (b) Behm, H.; Beurskens, P. T.; Plate, R.; Ottenheijm, H. C. J. Recl. Trav. Chim. Pays-Bas 1986, 105, 238.
18. (c) Still, I. W. J.; Strautmanis, J. R. Tetrahedron Lett. 1989, 30, 1041.
19. (d) Still, I. W. J.; Strautmanis, J. R. Can. J. Chem. 1990, 68, 1408.
20. (e) Kirkup, M. P.; Shankar, B. B.; McCombie, S.; Ganguly, A. K.; McPhail, A. T. Tetrahedron Lett. 1989 30, 6809.
21. Sandler, S. R.; Karo, W. Organic Functional Group Preparations; Academic Press: New York, 1989; Vol. 3, p 329.
22. (a) Benneche, T.; Strande, P.; Undheim, K. Synthesis 1983, 762.
23. (b) Kozikowski, A. P.; Wu, J.-P. Tetrahedron Lett. 1987, 28, 5125.
24. (a) Garner, P.; Park, J. M. Org. Synth. 1992, 70, 18.
25. (b) Dondoni, A.; Perrone, D. Org. Synth. 1999, 77, 64.
26. Kauffman, J. M.; Litak, P. T.; Boyko, W. T. J. Heterocycl. Chem. 1995, 32, 1541.
27. Mitsunobu, O. Synthesis 1981, 1.
28. Macor, J. E.; Ogilvie, R. J.; Wythes, M. J. Tetrahedron Lett. 1996, 37, 4289.
29. Compound 16 was prepared from N-hydroxyphthalimide in a three-step sequence. For details, see Supporting Information.
30. For a review, see: Kan, T.; Fukuyama, T. Chem. Commun. 2004, 353.
31. Olofson, R. A.; Martz, J. T.; Senet, J.-P.; Piteau, M.; Malfroot, T. J. Org. Chem. 1984, 49, 2081.