The synthesis of (±)-wilforonide

Synlett

Volumn , Issue 7, 1998, Pages 723-724

  Schkeryantz, Jeffrey M ^a   Luly, Jay R ^a   Coghlan, Michael J ^a  

^a ABBOTT LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

EID: 0007705262     PISSN: 09365214     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-1998-1769     Document Type: Article

References (23)

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2. Kutney, J. P.; Constabel, F.; Vasil, I. K. Cell Cult. Somatic Cell Genet. Plants 1988, 5, 159.
3. Kutney, J. P.; Han, K. Recl. Trav. Chim. Pays-Bas 1996, 115, 110.
4. Buckanin, R. S.; Chen, S. J.; Frieze, D. M.; Sher, F. T.; Berchtold, G. A. J. Am. Chem. Soc. 1980, 102, 1200.
5. Lai, C. K.; Buckanin, R. S.; Chen, S. J.; Zimmerman, D. F.; Sher, F. T.; Berchtold, G. A. J. Org. Chem. 1982, 47, 2364.
6. Garver, L. C.; Van Tamelen, E. E. J. Am. Chem. Soc. 1982, 104, 867.
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9. Lipsky. P. E.; Tao, X. L.; Cai, J.; Kovacs, W. J.; Olsen, N. J., U.S. Patent 5616458, 1997; Chem. Abstr. 1997, 126, 246818h.
10. Typically this type of process suffers from polyalkylation of the enolate derived from the monoalkylated product. A notable example relied on eneamine chemistry to efficiently monomethylate a closely analogous keto-ketal. See Piers, E.; Friesen, R. W. Can. J. Chem. 1992, 70, 1204.
11. Jung, M. E. Tetrahedron 1976, 32, 3.
12. Ellis, J. E.; Dutcher, J. S.; Heathcock, C. H. Synth. Commun. 1974, 4, 71.
13. Bodalski, R.; Pietrusiewicz, K. M.; Monkiewicz, J.; Koszuk, J. Tetrahedron Lett. 1980, 21, 2287.
14. Trost, B. M.; Kunz, R. A. J. Org. Chem. 1974, 39, 2648.
15. Ohta, S.; Shimabayashi, A.; Hatano, S.; Okamoto, M. Synthesis 1983, 715.
16. Zibuck, R.; Streiber, J. Org. Synth. 1993, 71, 236; see also references therein.
17. 6) 205.4, 176.8, 169.9, 68.8, 59.2, 51.4, 45.6, 42.4, 39.3, 38.2, 36.9, 32.0, 29.2, 26.8(3C), 21.9, 17.2 ppm.
18. McMurry, J. E.; Scott, W. J. Tetrahedron Lett. 1983, 24, 979.
19. Crisp, G. T.; Scott, W. J. Synthesis 1985, 335.
20. Crisp, G. T.; Meyer, A. G. J. Org. Chem. 1992, 57, 6972.
21. Molander, G. A.; Carey, J. S. J. Org. Chem. 1995, 60, 4845.
22. Ruthenium, sulfurane, and chromium-based oxidants returned or decomposed alcohol 9. Swern conditions provided the natural product albeit in low yield.
23. 13C NMR spectra of natural wilforonide. Spectra of the synthetic sample were also identical to those reported by Chen, K.; Yang, R.; Wang, C. Zhongcaoyao 1986, 17, 242.