Tandem organochromium-coupling and epoxide ring opening: A direct approach for the synthesis of cyclic ethers

Tetrahedron Letters

Volumn 41, Issue 20, 2000, Pages 3805-3807

  González, Isabel C ^a   Forsyth, Craig J ^a  

^a University of Minnesota   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ARTICLE; CHEMICAL ANALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; SYNTHESIS;

EID: 0343618785     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(00)00526-8     Document Type: Article

References (17)

1. (a) Boivin, T. L. B. Tetrahedron 1987, 43, 3309.
2. (b) Harmange, J.-C.; Figadère, B. Tetrahedron: Asymmetry 1993, 4, 1711.
3. (c) Koert, U. Synthesis, 1995, 115.
4. (d) Alvarez, E.; Candenas, M.-L.; Pérez, R.; Ravelo, J. L.; Delgado Martín, J. Chem. Rev. 1995, 95, 1953.
5. (a) Kishi, Y. Pure Appl. Chem 1992, 64, 343.
6. (b) Cintas, P. Synthesis 1992, 248.
7. (c) Wessjohann, L. A.; Scheid, G. Synthesis 1999, 1.
8. (d) Fürstner, A. Chem. Rev. 1999, 99, 991.
9. 3, THF-pyr, 82%; (iv) DIBAL, toluene, -78°C, 87%.
10. Gao, Y.; Hanson, R. M.; Klunder, J. M.; Ko, S. Y.; Masumune, H.; Sharpless, K. B. J. Am. Chem. Soc. 1987, 109, 5765.
11. Hara, S.; Dojo, H.; Takinami, S.; Suzuki, A. Tetrahedron Lett. 1983, 24, 731.
12. 1H NMR spectra of the corresponding (R)- and (S)-Mosher esters.
13. Stamos, D. P.; Sheng, C.; Chen, S. S.; Kishi, Y. Tetrahedron Lett. 1997, 38, 6355.
14. In the synthesis of asperdiol a distal epoxide directed a stereoselective organochromium-mediated bond formation: Still ,W. C.; Mobilio, D. J. Org. Chem. 1983, 48, 4785.
15. (a) Hoye, T. R.; Jenkins, S. A. J. Am. Chem. Soc. 1987, 109, 6196.
16. (b) Hashimoto, M.; Harigaya, H.; Yanagiya, M.; Shirahama, H. J. Org. Chem. 1991, 56, 2299.
17. (c) Lindel, T.; Franck, B. Tetrahedron Lett. 1995, 36, 9465.