Studies towards the total synthesis of cycloaraneosene and ophiobolin M: A general strategy for the construction of the 5-8 bicyclic ring system

European Journal of Organic Chemistry

Volumn , Issue 18, 2002, Pages 3145-3152

  Ruprah, Parminder K ^a   Cros, Jean Philippe ^a   Pease, J Elizabeth ^b   Whittingham, William G ^c   Williams, Jonathan M J ^a  

^a University of Bath Claverton Down   (United Kingdom)

^b ASTRAZENECA   (United Kingdom)

^c JEALOTT S HILL INTERNATIONAL RESEARCH CENTRE   (United Kingdom)

Author keywords

Fused ring systems; Natural products; Total synthesis

Indexed keywords

CYCLOARANEOSENE; DITERPENE; FUSICOCCIN; NATURAL PRODUCT; OPHIOBOLIN M; UNCLASSIFIED DRUG;

ARTICLE; CATALYSIS; DRUG ISOLATION; PARASITOSIS; STEREOCHEMISTRY; STRUCTURE ANALYSIS; SYNTHESIS; THERMODYNAMICS;

EID: 0036738714     PISSN: 1434193X     EISSN: None     Source Type: Journal    
DOI: 10.1002/1099-0690(200209)2002:18<3145::AID-EJOC3145>3.0.CO;2-3     Document Type: Article

References (26)

1. M. Rowley, M. Tsukamoto, Y. Kishi, J. Am. Chem. Soc. 1989, 111, 2735-2737; B. B. Snider, K. Yang, J. Org. Chem. 1992, 57, 3615-3626; L. A. Paquette, T. Z. Wang, N. H. Vo, J. Am. Chem. Soc. 1993, 115, 1676-1683.
2. M. Rowley, M. Tsukamoto, Y. Kishi, J. Am. Chem. Soc. 1989, 111, 2735-2737; B. B. Snider, K. Yang, J. Org. Chem. 1992, 57, 3615-3626; L. A. Paquette, T. Z. Wang, N. H. Vo, J. Am. Chem. Soc. 1993, 115, 1676-1683.
3. M. Rowley, M. Tsukamoto, Y. Kishi, J. Am. Chem. Soc. 1989, 111, 2735-2737; B. B. Snider, K. Yang, J. Org. Chem. 1992, 57, 3615-3626; L. A. Paquette, T. Z. Wang, N. H. Vo, J. Am. Chem. Soc. 1993, 115, 1676-1683.
4. A. Tsipouras, A. A. Adefarati, J. S. Tkacz, E. G. Frazier, S. P. Rhorer, E. Birzin, D. L. Zink, M. A. Goetz, S. B. Singh, J. M. Shaefer, Bioorg. & Med. Chem. 1996, 4, 531-536.
5. S. J. Miller, S.-H. Kim, Z.-R. Chen, R. H. Grubbs, J. Am. Chem. Soc. 1995, 117, 2108-2109.
6. Review: M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 37, 2037-2056; A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 3012-3043; D. Bourgeois, A. Pancrazi, L. Ricard, J. Prunet, Angew. Chem. Int. Ed. 2000, 39, 725-728.
7. Review: M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 37, 2037-2056; A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 3012-3043; D. Bourgeois, A. Pancrazi, L. Ricard, J. Prunet, Angew. Chem. Int. Ed. 2000, 39, 725-728.
8. Review: M. Schuster, S. Blechert, Angew. Chem. Int. Ed. Engl. 1997, 37, 2037-2056; A. Furstner, Angew. Chem. Int. Ed. 2000, 39, 3012-3043; D. Bourgeois, A. Pancrazi, L. Ricard, J. Prunet, Angew. Chem. Int. Ed. 2000, 39, 725-728.
9. Review: K. Ritter, Synthesis-Stuttgart 1993, 735-762.
10. Review: H. H. Shick, I Fichhorn, Synthesis 1989, 477-492.
11. M. L. Quesada, R. M. Schlessinger, W. H. Parsons, J. Org. Chem. 1978, 43, 3968-3970.
12. M. F. Schneider, H. Junka, S. Blechert, Tetrahedron 1995, 51, 13003-13014.
13. Review: N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757-5821; Review: G. Metha, V. Singh, Chem. Rev. 1999, 99, 881-930.
14. Review: N. A. Petasis, M. A. Patane, Tetrahedron 1992, 48, 5757-5821; Review: G. Metha, V. Singh, Chem. Rev. 1999, 99, 881-930.
15. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 6, 953-956; H. Katayama, H. Urushida, T. Nishioka, C. Wada, M. Nagao, F. Ozawa, Angew. Chem. Int. Ed. 2000, 39, 4513-4515.
16. M. Scholl, S. Ding, C. W. Lee, R. H. Grubbs, Org. Lett. 1999, 6, 953-956; H. Katayama, H. Urushida, T. Nishioka, C. Wada, M. Nagao, F. Ozawa, Angew. Chem. Int. Ed. 2000, 39, 4513-4515.
17. R. J. K Taylor, Organocopper Reagents, Oxford University Press, 1994.
18. J. A. Kozlowsky, in Comprehensive Organic Synthesis (Eds.: B. M. Trost, I. Fleming), Pergamon Press: Oxford, 1991; Vol. 4, Section 1.4.
19. P. Pelmutter, in Conjugate Addition Reactions in Organic Synthesis; Tetrahedron Organic Chemistry Series, Pergamon Press, 1992, Vol. 9.
20. Y. Yamamoto, Angew. Chem. Int. Ed. Engl. 1986, 25, 947-1038 and references therein.
21. Y. Yamamoto, K. Maruyama, J. Am. Chem. Soc. 1978, 100, 3240-3241.
22. S. Maratsuzawa, Y. Horiguchi, E. Nakamura, I. Kuwajima, Tetrahedron 1989, 45, 349-362.
23. J. E. McMurry, W. J. Scott, Tetrahedron Lett. 1980, 21, 4313-4316.
24. L. Novak, G. Baan, J. Marosfalvi, C. Szantay, Chem. Ber. 1980, 113, 2939-2949.
25. R. J. Greene, Mchem (Part 2) Thesis, 1997; T.-S. Li, J.-T. Li, H.-Z. Li, J. Chromatogr. A 1995, 715, 372-375.
26. R. J. Greene, Mchem (Part 2) Thesis, 1997; T.-S. Li, J.-T. Li, H.-Z. Li, J. Chromatogr. A 1995, 715, 372-375.