Enantioselective total syntheses of 13,14,15-isocrambescidin 800 and 13,14,15-isocrambescidin 657

Journal of the American Chemical Society

Volumn 122, Issue 20, 2000, Pages 4904-4914

  Coffey, D Scott ^a,b   Overman, Larry E ^a   Stappenbeck, Frank ^a,c  

^a UNIVERSITY OF CALIFORNIA   (United States)

^b ELI LILLY AND COMPANY   (United States)

^c ELAN PHARMACEUTICALS   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

13,14,15 ISOCRAMBESCIDIN; ALKALOID; ESTER; PHENYLACETIC ACID; PTILOMYCALIN A; TRIETHYLAMINE; UNCLASSIFIED DRUG;

ARTICLE; POLYMERIZATION; PROTON NUCLEAR MAGNETIC RESONANCE; SPONGE; STEREOCHEMISTRY; SYNTHESIS; TOPOGRAPHY;

EID: 0034709447     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja000235a     Document Type: Article

References (15)

1. Becerro, M. A.; Uriz, M. J.; Turon, X. Mar. Biol. 1994, 121, 301-307.
2. For a brief review of the biology and ecology of C. crambe, see: Berlinck, R. G. S. Nat. Prod. Rep. 1999, 16, 339-365.
3. Coffey, D. S.; McDonald, A. I.; Overman, L. E.; Rabinowitz, M. H.; Renhowe, P. A., preceding paper in this issue.
4. For reviews, see: (a) ref 3.
5. (b) Berlinck, R. G. S. Nat. Prod. Rep. 1996, 13, 377-409.
6. Berlinck, R. G. S. Prog. Chem. Org. Nat. Prod. 1995, 66, 119-295.
7. Faulkner, D. J. Nat. Prod. Rep. 1999, 16, 155-198, and earlier reviews in this series.
8. (a) Kashman, Y.; Hirsh, S.; McConnell, O. J.; Ohtani, I.; Kusumi, T.; Kakisawa, H. J. Am. Chem. Soc. 1989, 111, 8925-8926.
9. (b) Jares-Erijman, E. A.; Sakai, R.; Rinehart, K. L. J. Org. Chem. 1991, 56, 5712-5715.
10. Ohtani, I.; Kusumi, T.; Kakisawa, H.; Kashman, Y.; Hirsh, S. J. Am. Chem. Soc. 1992, 114, 8472-8479.
11. Ohtani, I.; Kusumi, T.; Kakisawa, H. Tetrahedron Lett. 1992, 33, 2525-2528.
12. (e) Tavares, R.; Daloze, D.; Braekman, J. C.; Hajdu, E.; Muricy, G.; Van Soest, R. W. M. Biochem. Syst. Ecol. 1994, 22, 645-646.
13. (f) Berlinck, R. G. S.; Braekman, J. C.; Daloze, D.; Bruno, I.; Riccio, R.; Ferri, S.; Spampinato, S.; Speroni, E. J. Nat. Prod. 1993, 56, 1007-1015.
14. Jares-Erijman, E. A.; Ingrum, A. L.; Carney, J. R.; Rinehart, K. L.; Sakai, R. J. Org. Chem. 1993, 58, 4805-4808.
15. Shi, J.-G.; Sun, F.; Rinehart, K. L. WO Patent 3,756,734, 1998.