Total synthesis of (-)-muscoride A

Journal of Organic Chemistry

Volumn 61, Issue 19, 1996, Pages 6517-6522

  Wipf, Peter ^a   Venkatraman, Srikanth ^a  

^a UNIVERSITY OF PITTSBURGH   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID;

ARTICLE; CHIRALITY; DRUG SYNTHESIS; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS;

EID: 0029847930     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo960891m     Document Type: Article

References (37)

1. Alfred P. Sloan Research Fellow, 1994-1996. NSF Presidential Faculty Fellow, 1994-1999. Camille Dreyfus Teacher-Scholar, 1995-1997.
2. For representative reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996,13, 75. (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Honkanen, R. E.; Boynton, A. L. In Protein Kinase C; Kuo, J. F., Ed.; Oxford University Press: Oxford, 1994; p 305. (d) Chem. Rev. 1993, 93, 1673-1944. (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1 and references cited therein.
3. For representative reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996,13, 75. (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Honkanen, R. E.; Boynton, A. L. In Protein Kinase C; Kuo, J. F., Ed.; Oxford University Press: Oxford, 1994; p 305. (d) Chem. Rev. 1993, 93, 1673-1944. (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1 and references cited therein.
4. For representative reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996,13, 75. (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Honkanen, R. E.; Boynton, A. L. In Protein Kinase C; Kuo, J. F., Ed.; Oxford University Press: Oxford, 1994; p 305. (d) Chem. Rev. 1993, 93, 1673-1944. (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1 and references cited therein.
5. For representative reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996,13, 75. (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Honkanen, R. E.; Boynton, A. L. In Protein Kinase C; Kuo, J. F., Ed.; Oxford University Press: Oxford, 1994; p 305. (d) Chem. Rev. 1993, 93, 1673-1944. (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1 and references cited therein.
6. For representative reviews, see: (a) Faulkner, D. J. Nat. Prod. Rep. 1996,13, 75. (b) Wipf, P. Chem. Rev. 1995, 95, 2115. (c) Honkanen, R. E.; Boynton, A. L. In Protein Kinase C; Kuo, J. F., Ed.; Oxford University Press: Oxford, 1994; p 305. (d) Chem. Rev. 1993, 93, 1673-1944. (e) Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1 and references cited therein.
7. Kato, Y.; Fusetani, N.; Matsunaga, S.; Hashimoto, K.; Fujita, S.; Furuya, T. J. Am. Chem. Soc. 1986, 108, 2780.
8. Searle, P. A.; Molinski, T. F. J. Am. Chem. Soc. 1995,117, 8126.
9. Carmeli, S.; Paik, S.; Moore, R. E.; Patterson, G.; Yoshida, W. Y. Tetrahedron Lett. 1993, 34, 6681.
10. Matsunaga, S.; Fusetani, N.; Hashimoto, K.; Koseki, K.; Noma, M.; Noguchi, H.; Sankawa, U. J. Org. Chem. 1989, 54, 1360.
11. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986,108, 846.
12. (a) Fusetani, N.; Yasumuro, K.; Matsunaga, S.; Hashimoto, K. Tetrahedron Lett. 1989, 30, 2809.
13. (b) Rashid, M. A.; Gustafson, K. R.; Cardellina, J. H.; Boyd, M. R. J. Nat. Prod. 1995, 58, 1120.
14. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc. 1991, 113, 3173.
15. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
16. Nagatsu, A.; Kajitani, H.; Sakakibara, J. Tetrahedron Lett. 1995, 36, 4097.
17. (a) Bayer, A.; Freund, S.; Nicholson, G.; Jung, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1336.
18. (b) Yorgey, P.; Lee, J.; Koerdel, J.; Vivas, E.; Warner, P.; Jebaratnam, D.; Kolter, R. Proc. Natl. Acad. Sci. U.S.A. 1994, 97, 4519.
19. 2
20. Natural products incorporating reverse prenyl groups at various indole ring positions are quite common. For example, see: (a) (Asterriquinone) Yamamoto, Y.; Nishimura, K; Kiriyama, N. Chem. Pharm. Bull. 1976, 24, 1853. (b) (Okaramine A.) Hayashi, H.; Takiuchi, K.; Murao, S.; Arai, M. Agric. Biol. Chem. 1989, 53, 461. (c) (Amauromine) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) (Gypsetin) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025.
21. Natural products incorporating reverse prenyl groups at various indole ring positions are quite common. For example, see: (a) (Asterriquinone) Yamamoto, Y.; Nishimura, K; Kiriyama, N. Chem. Pharm. Bull. 1976, 24, 1853. (b) (Okaramine A.) Hayashi, H.; Takiuchi, K.; Murao, S.; Arai, M. Agric. Biol. Chem. 1989, 53, 461. (c) (Amauromine) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) (Gypsetin) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025.
22. Natural products incorporating reverse prenyl groups at various indole ring positions are quite common. For example, see: (a) (Asterriquinone) Yamamoto, Y.; Nishimura, K; Kiriyama, N. Chem. Pharm. Bull. 1976, 24, 1853. (b) (Okaramine A.) Hayashi, H.; Takiuchi, K.; Murao, S.; Arai, M. Agric. Biol. Chem. 1989, 53, 461. (c) (Amauromine) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) (Gypsetin) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025.
23. Natural products incorporating reverse prenyl groups at various indole ring positions are quite common. For example, see: (a) (Asterriquinone) Yamamoto, Y.; Nishimura, K; Kiriyama, N. Chem. Pharm. Bull. 1976, 24, 1853. (b) (Okaramine A.) Hayashi, H.; Takiuchi, K.; Murao, S.; Arai, M. Agric. Biol. Chem. 1989, 53, 461. (c) (Amauromine) Marsden, S. P.; Depew, K. M.; Danishefsky, S. J. J. Am. Chem. Soc. 1994, 116, 11143. (d) (Gypsetin) Schkeryantz, J. M.; Woo, J. C. G.; Danishefsky, S. J. J. Am. Chem. Soc. 1995, 117, 7025.
24. (a) Wipf, P.; Venkatraman, S. J. Org. Chem. 1995, 60, 7224.
25. (b) Wipf, P.; Venkatraman, S. Synlett. in press.
26. Wipf, P.; Lim, S. J. Am. Chem. Soc. 1995, 117, 558.
27. Wipf, P.; Miller, C. P. J. Org. Chem. 1993, 58, 3604.
28. Anderson, G. W.; Zimmerman, J. E; Callaham, F. M. J. Am. Chem. Soc. 1967, 89, 5012.
29. Dess, D. B.; Martin, J. C. J. Am. Chem. Soc. 1991, 113, 7277.
30. Castro, B.; Dormoy, J. R.; Evin, G.; Selve, C. Tetrahedron Lett. 1975, 1219.
31. (a) Hennion, G. F.; Hanzel, R. S. J. Am. Chem. Soc. 1960, 82, 4908.
32. (b) Barmettler, P.; Hansen, H.-J. Helv. Chim. Acta 1990, 73, 1515.
33. Schmidt, U.; Lieberknecht, A.; Griesser, H.; Talbiersky, J. J. Org. Chem. 1982, 47, 3261.
34. Nakagawa, M. In The Chemistry of the Carbon-Carbon Triple Bond; Patai, S., Ed.; Wiley: New York, 1978; p 655.
35. 13C NMR of 1 and 20 are shown in the supporting information.
36. 2-Val-NHMe and Me-Val-NHMe are shown in the supporting information.
37. For a study of the metal-complexation properties of teroxazole segments of halichondramides, see: James, D. M,; Wintner, E.; Faulkner, D. J.; Siegel, J. S. Heterocycles 1993, 35, 675.