New oxidative tools for the functionalization of the cephalostatin North 1 hemisphere

Organic Letters

Volumn 5, Issue 13, 2003, Pages 2247-2250

  Lee, Jong Seok ^a   Fuchs, Philip L ^a  

^a PURDUE UNIVERSITY   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ACETAL DERIVATIVE; ALCOHOL DERIVATIVE; ANTINEOPLASTIC AGENT; CEPHALOSTATIN; DIMETHYLDIOXIRANE; KETONE DERIVATIVE; SILANE DERIVATIVE; UNCLASSIFIED DRUG; VINYL DERIVATIVE;

ARTICLE; CHEMICAL REACTION; CYCLIZATION; OXIDATION; STEREOCHEMISTRY; THERMODYNAMICS; X RAY ANALYSIS;

CYCLIZATION; EPOXY COMPOUNDS; ETHERS, CYCLIC; OXIDATION-REDUCTION; PHENAZINES; SPIRO COMPOUNDS; STEREOISOMERISM;

EID: 0141629765     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol034551g     Document Type: Article

References (29)

1. Cephalostatin Support Studies. 24. Oxidations. 2. For previous papers in these series, see ref 6 and: Lee, S. M.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 13978-13979.
2. Pettit, G. R.; Tan, R.; Xu, J.-P.; Ichihara, Y.; Williams, M. D.; Boyd, M. R. J. Nat. Prod. 1998, 61, 953 and references therein.
3. Fukuzawa, S.; Matsunaga, S.; Fusetani, N. J. Org. Chem. 1997, 62, 4484 and references therein.
4. LaCour, T. G.; Guo, C.; Ma, S.; Jeong, J. U.; Boyd, M. R.; Matsunaga, S. ; Fusetani, N.; Fuchs, P. L. Bioorg. Med. Chem. Lett. 1999, 9, 2587 and references therein. Leukemia, renal, and CNS lines are particularly sensitive to cephalostain 1.
5. Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828 and references therein. Jautelat, R.; Müller-Fahrnow, A.; Winterfeldt, E. Chem. Eur. J. 1999, 5, 1226. Basler, S.; Brunck, A.; Jautelat, R.; Winterfeldt, E. Helv. Chim. Acta, 2000, 83, 1854 and references therein.
6. Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828 and references therein. Jautelat, R.; Müller-Fahrnow, A.; Winterfeldt, E. Chem. Eur. J. 1999, 5, 1226. Basler, S.; Brunck, A.; Jautelat, R.; Winterfeldt, E. Helv. Chim. Acta, 2000, 83, 1854 and references therein.
7. Heathcock, C. H.; Smith, S. C. J. Org. Chem. 1994, 59, 6828 and references therein. Jautelat, R.; Müller-Fahrnow, A.; Winterfeldt, E. Chem. Eur. J. 1999, 5, 1226. Basler, S.; Brunck, A.; Jautelat, R.; Winterfeldt, E. Helv. Chim. Acta, 2000, 83, 1854 and references therein.
8. LaCour, T. G.; Guo, C.; Boyd, M. R.; Fuchs, P. L. Org. Lett. 2000, 2, 33.
9. Li, W.; LaCour, T. G.; Fuchs, P. L. J. Am. Chem. Soc. 2002, 124, 4548.
10. Lee, S. M.; Fuchs, P. L. Org. Lett. 2002, 4, 317. Lee, S. M.; LaCour, T. G.; Lantrip, D.; Fuchs, P. L. Org. Lett. 2002, 4, 313.
11. Lee, S. M.; Fuchs, P. L. Org. Lett. 2002, 4, 317. Lee, S. M.; LaCour, T. G.; Lantrip, D.; Fuchs, P. L. Org. Lett. 2002, 4, 313.
12. Betancor, C.; Freire, R.; Perez-Martin, I.; Prange, T.; Suarez, E. Org. Lett. 2002, 4, 1295.
13. LaCour, T. G.; Guo, C.; Bhandaru, S.; Boyd, M. R.; Fuchs, P. L. J. Am. Chem. Soc. 1998, 120, 692.
14. Barton, D. H. R.; Sammes, P. G.; Taylor, M. V.; Werstiuk, E. J. Chem. Soc. 1970, 1977. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Anal. Quim. 1971, 67, 903. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Tetrahedron 1972, 28, 1289.
15. Barton, D. H. R.; Sammes, P. G.; Taylor, M. V.; Werstiuk, E. J. Chem. Soc. 1970, 1977. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Anal. Quim. 1971, 67, 903. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Tetrahedron 1972, 28, 1289.
16. Barton, D. H. R.; Sammes, P. G.; Taylor, M. V.; Werstiuk, E. J. Chem. Soc. 1970, 1977. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Anal. Quim. 1971, 67, 903. Gonzalez, A. G.; Freire, R.; Garcia-Estrada, M. G.; Salazar, J. A.; Suarez, E. Tetrahedron 1972, 28, 1289.
17. 7 but the minor isomer is actually the C22β spiroketal and can be equilibrated quantitatively to the natural C22α configuration under acidic conditions (Lee, S. M. Unpublished results).
18. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
19. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
20. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
21. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
22. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
23. Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 124. Iida, T.; Yamaguchi, T.; Nakamori, R.; Hikosaka, M.; Mano, N.; Goto, J.; Nambara, T. J. Chem. Soc., Perkin Trans. 1 2001, 2229. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Dixon, J. T.; Holzapfel, C. W.; van Heerden, F. R. Synth. Commun. 1993, 23, 135. Bovicelli, P.; Lupattelli, P.; Fiorini, V.; Mincione, E. Tetrahedron Lett. 1993, 34, 6103. Bovicelli, P.; Lupattelli, P.; Fracassi, D.; Mincione, E. Tetrahedron Lett. 1994, 35, 935.
24. Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1989, 45, 7161. Ley, S. V. ; Anderson, J. C.; Blaney, W. M.; Jones, P. S.; Lidert, Z.; Morgan, E. D.; Robinson, N. G.; Santafianos, D.; Simmonds, M. S. J.; Toogood, P. L. Tetrahedron 1989, 45, 5175. Bernsmann, H.; Hungerhoff, B.; Fechner, R.; Fröhlich, R.; Metz, P. Tetrahedron Lett. 2000, 41, 1721.
25. Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1989, 45, 7161. Ley, S. V. ; Anderson, J. C.; Blaney, W. M.; Jones, P. S.; Lidert, Z.; Morgan, E. D.; Robinson, N. G.; Santafianos, D.; Simmonds, M. S. J.; Toogood, P. L. Tetrahedron 1989, 45, 5175. Bernsmann, H.; Hungerhoff, B.; Fechner, R.; Fröhlich, R.; Metz, P. Tetrahedron Lett. 2000, 41, 1721.
26. Ley, S. V.; Anthony, N. J.; Armstrong, A.; Brasca, M. G.; Clarke, T.; Culshaw, D.; Greck, C.; Grice, P.; Jones, A. B.; Lygo, B.; Madin, A.; Sheppard, R. N.; Slawin, A. M. Z.; Williams, D. J. Tetrahedron 1989, 45, 7161. Ley, S. V. ; Anderson, J. C.; Blaney, W. M.; Jones, P. S.; Lidert, Z.; Morgan, E. D.; Robinson, N. G.; Santafianos, D.; Simmonds, M. S. J.; Toogood, P. L. Tetrahedron 1989, 45, 5175. Bernsmann, H.; Hungerhoff, B.; Fechner, R.; Fröhlich, R.; Metz, P. Tetrahedron Lett. 2000, 41, 1721.
27. X-ray structural information relating to compounds 18, 20, and 26 can be obtained from the Cambridge Crystallographic Data Centre.
28. Jeong, J. U.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2431.
29. Kim, S.; Sutton, S. C.; Fuchs, P. L. Tetrahedron Lett. 1995, 36, 2427; see also ref 9.