Two-directional synthesis of polycyclopropanes. An approach to the quinquecyclopropane fragment of U-106305

Journal of Organic Chemistry

Volumn 62, Issue 5, 1997, Pages 1215-1222

  McDonald, W Scott ^a   Verbicky, Christopher A ^a   Zercher, Charles K ^a  

^a Univ of New Hampshire   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ANTILIPEMIC AGENT; CYCLOPROPANE DERIVATIVE; POLYMER; U 106305; UNCLASSIFIED DRUG;

ARTICLE; DRUG SYNTHESIS; IN VITRO STUDY; NUCLEAR MAGNETIC RESONANCE; REACTION ANALYSIS; STEREOCHEMISTRY;

EID: 0030932220     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo961136b     Document Type: Article

References (39)

1. Kuo, M. S.; Zielinski, R. J.; Cialdella, J. I.; Marschke, C. K.; Dupois, M. J.; Li, G. P.; Kloosterman, D. A.; Spilman, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629.
2. Yoshida, M.; Ezaki, M.; Hashimoto, M.; Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J. Antibiot. 1990, 43, 748-754.
3. (a) Falck, J. R.; Mekonnen, B.; Yu, J. Abstract of Papers, 209th National Meeting of the American Chemical Society, Anaheim, CA, 1995; American Chemical Society: Washington, DC, ORGN 57.
4. (b) Barren, A. G. M.; Kasdorf, K.; Tustin, G. J.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 1143.
5. Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J. J. Org. Chem. 1996, 61, 3280.
6. (a) Barrett, A, G. M.; Kasdorf, K.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1994, 1781.
7. (b) Barrett, A. G. M.; Doubleday, W. W.; Tustin, G. J.; White, A. J. P.; Williams, D. J. Chem. Soc., Chem. Commun. 1994, 1783.
8. (c) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357.
9. (d) Barrett, A. G. M.; Tustin, G. J. J. Chem. Soc., Chem. Commun. 1995, 357.
10. (e) Barrett, A. G. M.; Doubleday, W. W.; Kasdorf, K.; Tustin, G. J.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 407.
11. (f) Barrett, A. G. M.; Kasdorf, K.; White, A. J. P.; Williams, D. J. J. Chem. Soc., Chem. Commun. 1995, 649.
12. (g) Barrett, A. G. M.; Kasdorf, K. J. Chem. Soc., Chem. Commun. 1996, 325.
13. (h) Barrett, A. G. M.; Kasdorf, K. J. Am. Chem. Soc. 1996, 118, 11030.
14. (a) Barrett, A. G. M.; Hamprecht, D.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 7863.
15. (b) Charette, A.; Lebel, H. J. Am. Chem. Soc. 1996, 118, 10327.
16. (a) Schreiber, S. L. Chem. Scr. 1987, 27, 563.
17. (b) Poss, C. S.; Schreiber, S. L. Ace. Chem. Res. 1994, 27, 9.
18. (a) Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181.
19. (b) Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1995, 36, 5495.
20. Takacs, J. M.; Helle, M. A.; Seely, F. L. Tetrahedron Lett. 1986, 27, 1257.
21. (a) Furakawa, J.; Kawabata, N.; Nishimusa, J. Tetrahedron Lett. 1966, 3353.
22. (b) Furukawa, J.; Kawabata, N.; Nishimura, J. Tetrahedron 1968, 24, 53.
23. The structures were assigned by comparison to the NMR spectra of 4, 8, and 9 prepared subsequently.
24. (a) Charette, A. B.; Juteau, H. J. Am. Chem. Soc. 1994, 116, 2651.
25. (b) Charette, A. B.; Prescott, S.; Brochu, C. J. Org. Chem. 1995, 60, 1081.
26. Baumann, H.; Duthaler, R. O. Helv. Chim. Acta 1988, 71, 1025.
27. The TBDMS group was also shown to be an effective protecting group, with no difference in ee observed in the cyclopropanation reaction.
28. takahashi, H.; Yoshioka, M.; Ohno, M.; Kobayashi, S. Tetrahedron Lett. 1992, 33, 2575.
29. (a) dale, J. A.; Dull, L.; Mosher, H. S. J. Org. chem. 1969, 34, 2543.
30. 13C resonances for two of three cyclopropyl carbons base line resolution.
31. Ley, S. V.; Norman, J.; Griffith, W. P.; Marsden, S. P. Synthesis 1994, 639.
32. It is believed that decomposition of 6 was due to the presence of N-methylmorpholine, a byproduct of the TPAP/NMO oxidation reaction.
33. 13C resonances.
34. This is based upon the assumption that the third cyclopropanation reaction will proceed efficiently. Even though the diastereo-selective formation of the nonsymmetric tercyclopropane isomer 8 would not be negatively affected, the enantiomeric excess of 8 would be reduced.
35. Subsequent to our work, the successful purification of compounds 3 and 4 through crystallization has been reported. See ref 5.
36. Still, W. C.; Kahn, M.; Mitra, A. J. Org. Chem. 1978, 43, 2923.
37. Bissinger, W. E.; Fredenburg, R. H.; Kadesch, R. G.; Kung, F.; Langston, J. H.; Stevens, H. C.; Strain, F. J. Am. Chem. Soc. 1947, 69, 2955.
38. Pudovik, A. N. Zh. Obsch. Chim. 1949, 19, 1187.
39. Chaudhary, S. K.; Hernandez, O. Tetrahedron Lett. 1979, 95.