Highly regio- and stereospecific hydroxylation of C-1 position of 2- deacetoxytaxinine J derivative with DMDO

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3907-3910

  Horiguchi, Tohru ^a   Cheng, Qian ^a   Oritani, Takayuki ^a  

^a TOHOKU UNIVERSITY   (Japan)

Author keywords

Dioxiranes; Epoxidation; Epoxides; Hydroxylation; Regiospecificity; Stereospecificity; Taxoids

Indexed keywords

EPOXIDE; TAXOID;

ARTICLE; CHEMICAL BOND; CHEMICAL STRUCTURE; EPOXIDATION; HYDROXYLATION; NUCLEAR MAGNETIC RESONANCE; NUCLEAR OVERHAUSER EFFECT; OXIDATION; STEREOCHEMISTRY; STEREOSPECIFICITY;

EID: 0034697560     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00514-1     Document Type: Article

References (28)

1. Wani, M. C.; Taylor, H. L.; Wall, M. E.; Coggon, P.; McPhail, A. T. J. Am. Chem. Soc. 1971, 93, 2325-2327.
2. (a) Bissery, M. C.; Guénard, D.; Guéritte-Vogelein, F.; Lavelle, F. Cancer Res. 1991, 51, 4845-4848.
3. (b) Guénard, D.; Guéritte-Vogelein, F.; Potier, P. Acc. Chem. Res. 1993, 26, 160-167.
4. Schiff, P. B.; Fant, J.; Horwitz, S. B. Nature 1979, 227, 665-667.
5. Ojima, I.; Wang, T.; Miller, M. L.; Lin, S.; Borella, C. P.; Geng, X.; Pera, P.; Bernacki, R. Bioorg. Med. Chem. Lett. 1999, 9, 3423-3428.
6. Bosch, I.; Croop, J. Biochem. Biophys. Acta 1996, 1288, 37-54.
7. (a) Adam, W.; Bialas, J.; Hadjiarapoglou, L. Chem. Ber. 1991, 124, 2377.
8. (b) Ferrer, M.; Gilbert, M.; Sanchez-Baeza, F.; Messeguer, A. Tetrahedron Lett. 1996, 37, 3585-3586.
9. (a) Cheng, Q.; Oritani, T.; Horiguchi, T. Tetrahedron, 1999, 55, 12 099-12 108.
10. (b) Cheng, Q.; Oritani, T.; Horiguchi, T.; Yamada, T.; Hassner, A. Tetrahedron 2000, 56, 1181-1192.
11. (c) Cheng, Q.; Oritani, T.; Horiguchi, T.; Yamada, T.; Mong, Y. Bioorg. Med. Chem. Lett. 2000, 10, 517-521.
12. (d) Cheng, Q.; Oritani, T.; Horiguchi, T. Tetrahedron 2000, 56, 1667-1679.
13. (e) Cheng, Q.; Oritani, T.; Horiguchi, T. Chin. Chem. Lett. 2000, 11, in press.
14. Liang, J.-Y.; Min, Z.-D.; Niwa, M. Acta Chim. Sin. 1988, 46, 1053-1055.
15. Alloatti, G.; Penna, C.; Levi, R. C.; Gallo, M. P.; Appendino, G.; Fenoglio, I. Life Sci. 1996, 58, 845-852.
16. Bathini, Y.; Micetich, A. G.; Daneshtalab, M. Synth. Commun. 1994, 24, 1513-1517.
17. Hosoyama, H.; Shigemori, H.; In, Y.; Ishida, T.; Kobayashi, J. Tetrahedron 1998, 54, 2521-2528.
18. 3) δ: 171.3 (s), 171.1 (s), 170.4 (s), 169.9 (s), 140.7 (s), 135.1 (s), 76.9 (d), 76.5 (s), 73.8 (d), 72.0 (d), 71.5 (s), 70.1 (s), 61.5 (s), 48.6 (t), 47.2 (s), 44.9 (s), 40.6 (t), 37.2 (t), 36.1 (d), 32.4 (t), 28.3 (q), 22.5 (q), 22.1, 22.0, 21.7, 21.6 (4×q), 18.1 (q), 15.7 (s), 6.7 (q), 4.6 (t).
19. The comparisons of the NOE data of 6 and 7 with those of the closely related natural and semisynthetic 1β-OH-taxoids exhibit if the 1-hydroxy is α-orientated; there should be strong NOE relationships between H-2β and H-14β, and between H-3α and H-14α. These are confirmed by the molecular model studies. In fact, to our knowledge, so far all natural and semisynthetic 1-OH taxoids having been reported are β-orientated. In addition, it is unreasonable to think about a very steric 1-α-hydroxyl form in a rigid taxane skeleton by an analysis of molecular model.
20. Hill, C. L. In Advances in Oxygenated Processes, Baumstark, A. L., Ed.; JAI: Greenwich, CT, 1988; pp. 1-30.
21. Giamalva, D. H.; Church, D. F.; Pryor, W. A. J. Org. Chem. 1988, 53, 3429-3432.
22. Once a radical-pair is produced from state I, both radicals might diffuse out of the cage. However, the formation of a pair of separate radicals can be rejected because of the observed complete retention of configuration and no products derived from free radical reactions, or even arising from the radical-initiated chain decomposition of dioxirane itself; these corroborate that discrete free radicals are not involved in this O-atom insertion.
23. Bach, R. D.; Andres, J. L.; Owensby, A. L.; Schlegel, H. B.; McDouall, J. J. W. J. Am. Chem. Soc. 1992, 114, 7207-7217.
24. (a) Murray, R. W.; Jeyaraman, R.; Mohan, L. J. Am. Chem. Soc. 1986, 108, 2470-2472.
25. (b) Mello, R.; Cassidei, L.; Fiorentino, M.; Fusco, C.; Curci, R. Tetrahedron Lett. 1990, 31, 3067-3070.
26. (c) Adam, A.; Asensio, G.; Curci, R.; Gonzales-Nunez, M. E.; Mello, R. J. Org. Chem. 1992, 57, 953-955.
27. (d) Curci, R.; Dinoi, A.; Rubino, M. F. Pure Appl. Chem. 1995, 67, 811-822.
28. Hu, S.; Sun, D.; Tian, X.; Fang. Q. Tetrahedron Lett. 1997, 38, 2721-2724.