Stereoselective synthesis of highly-functionalized cyclohexene derivatives having a diethoxyphosphoryldifluoromethyl functionality from cyclohex-2-enyl-1-phosphates

Synlett

Volumn , Issue 10, 2003, Pages 1407-1410

  Yokomatsu, Tsutomu ^a   Kato, Junya ^a   Sakuma, Chiseko ^a   Shibuya, Shiroshi ^a  

^a TOKYO UNIVERSITY OF PHARMACY AND LIFE SCIENCES   (Japan)

Author keywords

Diastereoselectivity; Fluorine; Phosphonates; Regioselectivity

Indexed keywords

BROMINE DERIVATIVE; CYCLOHEXANE DERIVATIVE; CYCLOHEXENE DERIVATIVE; DIETHOXYPHOSPHORYLDIFLUOROMETHYLZINC BROMIDE; METHYL GROUP; UNCLASSIFIED DRUG;

ARTICLE; CHEMICAL REACTION; STEREOCHEMISTRY;

EID: 0041386583     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2003-40862     Document Type: Article

References (44)

1. Hunter, T. Cell 2000, 100, 113.
2. (a) Blackburn, G. M. Chem. Ind. (London) 1981, 134.
3. (b) Blackburn, G. M.; Kent, D. E.; Kolmann, F. J. Chem. Soc., Perkin Trans. 1 1984, 1149.
4. (c) O'Hagan, D.; Rzepa, H. S. Chem. Commun. 1997, 645.
5. (d) Thatcher, G. R.; Campbell, A. S. J. Org. Chem. 1993, 58, 2272.
6. (e) Taylor, S. D.; Kotoris, C. C.; Hum, G. Tetrahedron 1999, 55, 12431.
7. (f) Burton, D. J.; Yang, Z.-Y. Tetrahedron 1992, 48, 189.
8. (a) Herpin, T. F.; Motherwell, W. B.; Roberts, B. P.; Roland, S.; Weibel, J.-M. Tetrahedron 1997, 53, 15085.
9. (b) Yokomatsu, T.; Murano, T.; Suemune, K.; Shibuya, S. Tetrahedron 1997, 53, 815.
10. (c) Yokomatsu, T.; Abe, H.; Sato, M.; Suemune, K.; Kihara, T.; Soeda, S. ; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 1998, 6, 2495.
11. (d) Yokomatsu, T.; Murano, T.; Umesue, I.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. Lett. 1999, 9, 529.
12. (e) Shakespeare, W. C.; Bohacek, R. S.; Narula, S. S.; Azimioara, D.; Yuan, R. W.; Dalgarno, D. C.; Madden, L. M. C.; Holt, D. A. Bioorg. Med. Chem. Lett. 1999, 9, 3109.
13. (f) Yokomatsu, T.; Hayakawa, Y.; Kihara, T.; Koyanagi, S.; Soeda, S.; Shimeno, H.; Shibuya, S. Bioorg. Med. Chem. 2000, 8, 2571.
14. (g) Otaka, A.; Mitsuyama, E.; Kinoshita, T.; Tamamura, H.; Fujii, N. J. Org. Chem. 2000, 65, 4888.
15. (h) Berkowitz, D. B.; Bose, M.; Pfannenstiel, T. J.; Doukov, T. J. Org. Chem. 2000, 65, 4498.
16. (i) Lopin, C.; Gautier, A.; Gouhier, G.; Piettre, S. R. J. Am. Chem. Soc. 2002, 124, 14668.
17. (a) Blades, K.; Lapotre, D.; Percy, J. M. Tetrahedron Lett. 1997, 38, 5895.
18. (b) Blades, K.; Lequeux, T. P.; Percy, J. M. Chem. Commun. 1996, 1457.
19. (c) Yokomatsu, T.; Katayama, S.; Shibuya, S. Chem. Commun. 2001, 1878.
20. (d) Butt, A. H.; Kariuki, B. M.; Percy, J. M.; Spencer, N. S. Chem. Commun. 2002, 682.
21. (a) Campbell, A. S.; Thatcher, G. R. J. Tetrahedron Lett. 1991, 32, 2207.
22. (b) Potter, B. V. L.; Lampe, D. Angew. Chem., Int. Ed. Engl. 1995, 34, 1933.
23. (c) Hinterding, K.; Alondo-Díaz, D.; Waldmann, H. Angew. Chem. Int. Ed. 1998, 37, 688.
24. (d) Miller, D. J.; Beaton, M. W.; Wilkie, J.; Gani, D. Chembiochem 2000, 1, 262.
25. (a) Yokomatsu, T.; Suemune, K.; Murano, T.; Shibuya, S. J. Org. Chem. 1996, 61, 7207.
26. (b) Sprague, L. G.; Burton, D. J.; Guneratne, R. D.; Bennett, W. E. J. Fluorine Chem. 1990, 49, 75.
27. (c) Zhang, X.; Burton, D. J. Tetrahedron Lett. 2000, 41, 7791.
28. (a) Yokomatsu, T.; Ichimura, A.; Kato, J.; Shibuya, S. Synlett 2001, 287.
29. (b) Burton, D. J.; Sparague, L. G. J. Org. Chem. 1989, 54, 613.
30. Harris, K. J.; Gu, Q.-M.; Sih, Y.-E.; Cirdaukas, G.; Sih, C. Tetrahedron Lett. 1991, 32, 3941.
31. 7b
32. trans-Isomer i of 4c reacted with 2 under the same conditions to give a 62:38 mixture of α-alkylated product ii and γ-alkylated product iii in 71% yield (Scheme 5). The α-alkylated product showed virtually no de. However, the γ-alkylated product showed modest de preferable to 1,2-trans-stereochemistry showing that the reaction proceeded from the less-hindered syn-face of the phosphate to avoid the bulky pivaloyl group.
33. Compounds 5c and 6c were not readily separated on column chromatography on silica gel. However, these products were also separated by using the difference in their chemical reactivity; selective deprotection of the Piv functional group of 5d occurred to give 6b upon treatment with ethylmagnesium bromide in diethyl ether at -15 °C.
34. abstract
35. 2O, pyridine, PivCl, pyridine).
36. Chin, Y.; Levy, G. C. J. Am. Chem. Soc. 1984, 106, 6533.
37. Jørgensen, M.; Iversen, E. H.; Paulsen, A. L.; Madsen, R. J. Org. Chem. 2001, 66, 4630.
38. 3P, THF). The sign of the specific rotation was identical to that of the authentic specimen prepared by resolution of (±)-14 according to the method of Chung, see: Kwon, Y.-U.; Chung, S.-K. Org. Lett. 2001, 3, 3013.
39. 2). In the osmium oxidation, 12b was rapidly dihydoxylated but 13b remained unreacted to be isolated by column chromatography. The details will be described elsewhere.
40. (a) Liu, Z.; Classon, B.; Samuelsson, B. J. Org. Chem. 1990, 55, 4273.
41. (b) Pakulski, Z.; Zamojski, A. Carbohydr. Res. 1990, 205, 410.
42. (c) Garegg, P. J. Synthesis 1979, 469.
43. See the reference in note 16.
44. Stereo- and regiochemistry of 20c was confirmed by 2D-NMR including HMBC, HMQC, COSY and NOESY.