Oligocyclopropane structural units from cationic intermediates

Organic Letters

Volumn 1, Issue 8, 1999, Pages 1257-1260

  Taylor, Richard E ^a   Conrad Engelhardt, F ^a   Yuan, Haiqing ^a  

^a UNIVERSITY OF NOTRE DAME   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0001383633     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol990221d     Document Type: Article

References (36)

1. Yoshida, M.; Ezaki, M.; Hashimoto, M.; Yamashita, M.; Shigematsu, N.; Okuhara, M.; Kohsaka, M.; Horikoshi, K. J. Antibiot. 1990, 43, 748-754.
2. Kuo, M. S.; Zielinski, R. J.; Cialdella, J. I.; Marschke, C. K.; Dupuis, M. J.; Li, G. P.; Kloosterman, D. A.; Spilmann, C. H.; Marshall, V. P. J. Am. Chem. Soc. 1995, 117, 10629-10634.
3. For papers describing the total synthesis of FR-900848, see: (a) Barrett A. G. M.; Kasdorf, K. J. Chem. Soc. Chem. Commun. 1996, 325-326.
4. (b) Barrett A. G. M.; Kasdorf, K. J. Am. Chem. Soc. 1996, 118, 11030-11037.
5. (c) Falck, J. R.; Mekonnen, B.; Yu, J.; Lai, J.-Y. J. Am. Chem. Soc. 1996, 118, 6096-6097.
6. For the total synthesis of U-106305, see: (a) Barrett, A. G. M.; Hamprecht, D.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1996, 118, 7863-7864.
7. (b) Barrett, A. G. M.; Hamprecht, D.; White, A. J. P.; Williams, D. J. J. Am. Chem. Soc. 1997, 119, 8608-8615.
8. (c) Charette, A. B.; Lebel, H. J. Am. Chem. Soc: 1996, 118, 10327-10328.
9. For alternative approaches to oligocyclopropane structural units using modified Simmons-Smith technology on cyclopropyl-substituted alkenes, see: (a) McDonald, W. S.; Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 1997, 63, 1215-1222.
10. (b) Therberge, C. R.; Verbicky, C. A.; Zercher, C. K. J. Org. Chem. 1996, 62, 8792-8798.
11. (c) Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1995, 36, 5495-5498.
12. (d) Armstrong, R. W.; Maurer, K. W. Tetrahedron Lett. 1995, 36, 357-360.
13. (e) Theberge, C. R.; Zercher, C. K. Tetrahedron Lett. 1994, 35, 9181.
14. For additional examples oligocyclopropane preparation, see: (a) Itoh, T.; Emoto, S.; Kondo, M.; Tetrahedron 1998, 54, 5225-5232.
15. (b) Charette, A. B.; DeFreitas-Gil, R. P. Tetrahedron Lett. 1997, 38, 2809-2812.
16. (c) Cebula, R. E. J.; Hanna, M. R.; Theberge, C. R.; Verbicky, C. A.; Zercher, C. K. Tetrahedron Lett. 1996, 37, 8341.
17. (d) O'Bannon, P. E.; Dailey, W. P. J. Am. Chem. Soc. 1989, 111, 9244-9245.
18. Taylor, R. E.; Ameriks, M. K.; LaMarche, M. J. Tetrahedron Lett. 1997, 38, 2057-2060.
19. For examples of chemical approaches to cyclopropanes via cyclo-propylcarbinyl cationic intermediates, see: (a) Krief, A.; Provins, L. Synlett 1997, 505-507.
20. (b) Hannesian, S.; Reinhold, U.; Ninkovic, S. Tetrahedron Lett. 1996, 37, 8971-8974.
21. (c) White, J. D.; Jensen, M. S Synlett 1996, 31.
22. (d) White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1995, 117, 6224.
23. (e) Nagasawa, T.; Hana, Y.; Onoguchi, Y.; Ohba, S.; Suzuki, S. Synlett 1995, 739.
24. (f) White, J. D.; Jensen, M. S. J. Am. Chem. Soc. 1993, 115, 2970.
25. Schaumann has previously reported the preparation of vinylcyclopropanes from similar starting materials through an allylic anion-mediated process. For a lead reference, see: Schaumann, E.; Kirschning, A.; Narjes, F. J. Org. Chem. 1991, 56, 717-723.
26. For the preparation of olefinic diols via similar silyloxycycloalkenes, see: Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760. For the preparation of tetrahydrofurans and pyrans via similar silyloxycycloalkenes, see: Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861-7864.
27. For the preparation of olefinic diols via similar silyloxycycloalkenes, see: Chang, S.; Grubbs, R. H. Tetrahedron Lett. 1997, 38, 4757-4760. For the preparation of tetrahydrofurans and pyrans via similar silyloxycycloalkenes, see: Meyer, C.; Cossy, J. Tetrahedron Lett. 1997, 38, 7861-7864.
28. (a) Keck, G. E.; Geraci, L. S. Tetrahedron Lett. 1993, 34, 7827-7828.
29. (b) Racherla, U. S.; Brown, H. C. J. Org. Chem. 1991, 56, 401-404.
30. (c) Roush, W. R.; Hoong, L. K.; Palmer, M. A. J.; Park, J. C. J. Org. Chem. 1990, 55, 4109-4117.
31. The relative stereochemistry of the diastereomeric homoallylic alcohols 9a and 9b was determined by chemical correlation to previously reported compounds. See: Mohapatra, D. K.; Datta, A. J. Org. Chem. 1998, 63, 642-646.
32. (a) We have more recently repeated these experiments and have shown that the phenoxy series is ∼80% stereospecific. (b) We do not believe that the benzyl ether has an effect on the initial cyclopropanation reaction (7 to 8, Scheme 2).
33. The "classic" and "nonclassic" carbocationic behavior of homoallyl-cyclopropyl carbinyl-cyclobutyl cations has recently been reviewed: Olah, G. A.; Reddy, V. P.; Surya Prakash, G. K. Chem. Rev. 1992, 92. 69-95. For a seminal discussion of these intermediates, see: Roberts J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 2509.
34. The "classic" and "nonclassic" carbocationic behavior of homoallyl-cyclopropyl carbinyl-cyclobutyl cations has recently been reviewed: Olah, G. A.; Reddy, V. P.; Surya Prakash, G. K. Chem. Rev. 1992, 92. 69-95. For a seminal discussion of these intermediates, see: Roberts J. D.; Mazur, R. H. J. Am. Chem. Soc. 1951, 73, 2509.
35. Jeffery, T.; Gueugnot, S.; Linstrumelle, G. Tetrahedron Lett. 1992, 33, 5757-5760.
36. Johnson, W. S. Acc. Chem. Res. 1968, 54, 4731.