CP-225,917 and CP-263,114 synthesis support studies: Testing a radical cyclization strategy for installation of the side-chains

Australian Journal of Chemistry

Volumn 56, Issue 6, 2003, Pages 577-583

  Banwell, Martin G ^a   Coster, Mark J ^a   Edwards, Alison J ^a   Vögtle, Markus ^a  

^a AUSTRALIAN NATIONAL UNIVERSITY   (Australia)

Author keywords

[No Author keywords available]

Indexed keywords

FREE RADICAL REACTIONS; MATERIALS TESTING; MOLECULAR STRUCTURE; NEGATIVE IONS; STEREOCHEMISTRY; SYNTHESIS (CHEMICAL);

ALLYLATION SEQUENCE; ALLYLTRIBUTYLSTANNANE; HEXABUTYLDISTANNANE HYDRIDE; LACTONE; RADICAL CYCLIZATION STRATEGY; SELENOCARBONATE; SIDE CHAINS;

ORGANIC COMPOUNDS;

EID: 0037810393     PISSN: 00049425     EISSN: None     Source Type: Journal    
DOI: 10.1071/CH02244     Document Type: Article

References (26)

1. T. T. Dabrah, H. J. Harwood, Jr., L. H. Huang, N. D. Jankovich, T. Kaneko, J.-C. Li, S. Lindsey, P. M. Moshier, T. A. Subashi, M. Therrien, P. C. Watts, J. Antibiot. 1997, 50, 1.
2. The structures of compounds (1) and (2) seem to have been revealed for the first time in 1995-see Chem. Eng. News 1995 (May 22nd), 29.
3. T. T. Dabrah, T. Kaneko, W. Massefski Jnr., E. B. Whipple, J. Am. Chem. Soc. 1997, 119, 1594.
4. For excellent reviews on the "CP compounds", including studies directed towards their synthesis, see: (a) U. Deiderichsen, Nachr. Chem. Tech. Lab. 1999, 47, 1423.
5. (b) D. Hepworth, Chem. Ind. (London), 2000, 59.
6. (c) J. T. Starr, E. M. Carreira, Angew. Chem. Int. Ed. 2000, 39, 1415.
7. (d) K. C. Nicolaou, P. S. Baran, Angew. Chem. Int. Ed. 2002, 41, 2678.
8. (a) K. C. Nicolaou, J. Jung, W. J. Yoon, K. C. Fong, H.-S. Choi, Y. He, Y.-L. Zhong, P. S. Baran, J. Am. Chem. Soc. 2002, 124, 2202. and references therein.
9. (b) C. Chen, M. E. Layton, S. M. Sheehan, M. D. Shair, J. Am. Chem. Soc. 2000, 122, 7424.
10. (c) Q. Tan, S. J. Danishefsky, Angew. Chem. Int. Ed. 2000, 39, 4509, and references therein.
11. (d) N. Waizumi, T. Itoh, T. Fukuyama, J. Am. Chem. Soc. 2000, 122, 7825.
12. K. C. Nicolau, J.-K. Jung, W. H. Yoon, Y. He, Y.-L. Zhong, P. S. Baran, Angew. Chem. Int. Ed. 2000, 39, 1829.
13. M. G. Banwell, K. J. McRae, A. C. Willis, J. Chem. Soc., Perkin Trans. 1 2001, 2194.
14. M. D. Bachi, E. Bosch, J. Org. Chem. 1992, 57, 4696.
15. A. K. Singh, R. K. Bakshi, E. J. Corey, J. Am. Chem. Soc. 1987, 109, 6187.
16. D. L. J. Clive, H. W. Manning, T. L. B. Boivin, M. H. D. Postema, J. Org. Chem. 1993, 58, 6857.
17. B. Sire, S. Seguion, S. Z. Zard, Angew. Chem. Int. Ed. 1998, 37, 2864.
18. J. B. Lambert, A. G. Holcomb, J. Am. Chem. Soc. 1971, 93, 3952.
19. M. A. Lucas, O. T. K. Nguyen, C. H. Schiesser, S.-L. Zheng, Tetrahedron 2000, 56, 3995.
20. D. J. Watkin, C. K. Prout, L. J. Pearce, Cameron 1996 (Chemical Crystallogrphy Laboratory: Oxford).
21. V. VanRheenen, R. C. Kelly, D. Y. Cha, Tetrahedron Lett., 1976, 1973.
22. Z. Otwinowski, W. Minor, in Methods in Enzymology (Eds. C. W. Carter Jr., R. M. Sweet) 1997, Vol. 276, pp. 307-326 (Academic Press: New York, NY).
23. P. Coppens, in Crystallographic Computing (Eds. F. R. Ahmed, S. R. Hall, C. P. Huber), 1970, pp. 255-270 (Munksgaard: Copenhagen).
24. A. Altomare, M. C. Burla, M. Cammali, G. L. Cascarano, C. Giacovazzo, A. Guagliardi, A. G. G. Mollterni, G. Polidori, R. Spagna, J. Appl. Crystallogr. 1999, 32, 115.
25. (a) J. R. Carruthers, D. J. Watkin, Acta Cryst. 1979, A35, 698.
26. (b) D. J. Watkin, C. K. Prout, J. R. Carruthers, P. W. Betteridge, Crystals ver. 10 1996 (Chemical Crystallography Laboratory Oxford).