Total synthesis of (-)-muscoride A: A novel bis-oxazole based alkaloid from the cyanobacterium Nostoc muscorum

Synthesis

Volumn , Issue SPEC. ISS. APR., 1998, Pages 613-618

  Muir, James C ^c   Pattenden, Gerald ^a   Thomas, Roy M ^b  

^a UNIVERSITY OF NOTTINGHAM   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c NONE

Author keywords

Bis oxazole; Muscoride A

Indexed keywords

ALKALOID; MUSCORIDE A; UNCLASSIFIED DRUG; ANTIBIOTIC AGENT;

ANTIBACTERIAL ACTIVITY; ARTICLE; CHEMICAL STRUCTURE; CYANOBACTERIUM; CYCLIZATION; ESTERIFICATION; NOSTOC; NOSTOC MUSCORUM; PROTON NUCLEAR MAGNETIC RESONANCE; STEREOCHEMISTRY; SYNTHESIS; DRUG CONFORMATION; DRUG ISOLATION; DRUG SYNTHESIS; STRUCTURE ACTIVITY RELATION;

EID: 0031597448     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-5934     Document Type: Article

References (25)

1. Nagatsu, A.; Kajitani, H.; Sakakibara, J. Tetrahedron Lett. 1995, 36, 4097.
2. Ichiba, T.; Yoshida, W. Y.; Scheuer, P. J.; Higa, T.; Gravalos, D. G. J. Am. Chem. Soc. 1991, 113, 3173.
3. For synthetic studies with this compound, see: Barrett, A. G. M.; Kohrt, J. T. Synlett 1995, 415.
4. Wipf, P.; Lim, S. Chimia 1996, 50, 157.
5. Cheng, Z. Z.; Hamada, Y.; Shioiri, T. Synlett 1997, 109.
6. Lindquist, N.; Fenical, W.; Van Duyne, G. D.; Clardy, J. J. Am. Chem. Soc. 1991, 113, 2303.
7. Roesener, J. A.; Scheuer, P. J. J. Am. Chem. Soc. 1986, 108, 846.
8. Jansen, R.; Kunze, B.; Reichenback, H.; Jurkiewicz, E.; Hunsmann, G.; Höfle, G. Liebigs Ann. Chem. 1992, 357.
9. Knight, D. W.; Pattenden, G.; Rippon, D. E. Synlett 1990, 36.
10. Martin, B. J.; Clough, J. M.; Pattenden, G.; Waldron, I. R. Tetrahedron Lett. 1993, 34, 5151.
11. Boden, C. D. J.; Pattenden, G. Tetrahedron Lett. 1994, 35, 8271.
12. Boden, C. D. J.; Pattenden, G. Tetrahedron Lett. 1995, 36, 6153.
13. Boyce, R. J.; Pattenden, G. Tetrahedron 1995, 51, 7313.
14. Boyce, R. J.; Mulqueen, G. C.; Pattenden, G. Tetrahedron 1995, 51, 7321.
15. Boden, C. D. J.; Norley, M. C.; Pattenden, G. Tetrahedron Lett. 1996, 37, 9111.
16. Chattopadhyay, S. K.; Pattenden, G. Synlett 1997, 1341 and 1345.
17. Michael, J. P.; Pattenden, G. Angew. Chem., Int. Ed. Engl. 1993, 32, 1.
18. Wipf, P.; Venkatraman, S. J. Org. Chem., 1996, 61, 6517.
19. Tanaka, T.; Nakajima, K.; Okawa, K. Bull. Chem. Soc. Jpn. 1980, 53, 1352.
20. Imada, Y.; Yuasa, M.; Nakamura, I.; Murahashi, S. J. Org. Chem. 1994, 59, 2282.
21. Atkins, G. M.; Burgess, E. M. J. Am. Chem. Soc. 1968, 90, 4744.
22. Wipf, P.; Miller, C. P. Tetrahedron. Lett. 1992, 33, 907.
23. Videnov, G.; Kaiser, D.; Kempter, C.; Jung, G. Angew. Chem., Int. Ed. Engl. 1996, 35, 1503.
24. Coste, J.; Le-Nguyen, D.; Castro, B. Tetrahedron Lett. 1990, 31, 205.
25. Lafargue, P.; Guenot, P.; Lellouche, J. Heterocycles 1995, 41, 947.