Selective oxidation of primary silyl ethers and its application to the synthesis of natural products

Tetrahedron Letters

Volumn 40, Issue 28, 1999, Pages 5161-5164

  Rodriguez A ^a   Nomen, M ^a   Spur, B W ^a   Godfroid, J J ^b  

^a UMDNJ School of Osteopathic Medicine   (United States)

^b Laboratoire de Pharmacochimie   (France)

Author keywords

[No Author keywords available]

Indexed keywords

ALDEHYDE; ETHER DERIVATIVE; HYDROXYICOSATETRAENOIC ACID; LEUKOTRIENE B4;

ARTICLE; CHIRALITY; OXIDATION; STEREOCHEMISTRY; SYNTHESIS;

EID: 0033538635     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4039(99)00956-9     Document Type: Article

References (31)

1. Tomioka, H.; Takai, K.; Oshima, K.; Nozaki, H. Tetrahedron Lett. 1981, 22, 1605-1608.
2. de Nooy, A. E. J.; Besemer, A. C.; Bekkum H. v. Synthesis 1996, 1153-1174.
3. Nicolaou, K. C.; Veale, C. A.; Webber, S. E.; Katerinopoulos. J. Am. Chem. Soc. 1985, 107, 7515-7518.
4. Nicolaou, K. C.; Webber, S. E. Synthesis 1986, 453-461.
5. Lee, A. S.-Y; Yeh, H.-C.; Shie, J.-J. Tetrahedron Lett. 1998, 39, 5249-5252.
6. Muzart, J. Synthesis 1993, 11-27.
7. Mahrwald, R.; Theil, F.; Schick, H.; Schwarz, S.; Palme, H.-J.; Weber, G. J. Prakt. Chem. 1986, 328, 777-783.
8. Mahrwald, R.; Theil, F.; Schick, H.; Palme, H.-J.; Nowak, H.; Weber, G.; Schwarz, S. Synthesis 1987, 1012-1013.
9. Mancuso, A. J.; Swern, D. Synthesis 1981, 165-185.
10. Tolstikov, G. A.; Miftakhov, M. S.; Adler, M. E.; Komissarova, N. G.; Kuznetsov, O. M.; Vostrikov, N. S. Synthesis 1989, 940-942.
11. Tolstikov, G. A.; Miftakhov, M. S.; Alde, M. E.; Valeev, F. A.; Vostrikov, N. S. Zh. Org. Khim. 1987, 23, 1564-1565.
12. Mahrwald, R.; Schick, H.; Vasil' Eva, L. L.; Pivnitsky, K. K.; Weber, G.; Schwarz, S. J. Prakt. Chem. 1990, 332, 169-175.
13. Tidwell, T. T. Synthesis 1990, 857-870.
14. Tolstikov, G. A.; Miftakhov, M. S.; Vostrikov, N. S.; Komissarova, N. G.; Adler, M. E.; Kuznetsov, O. M. Zh. Org. Khim. 1988, 24, 224-225.
15. Afonso, C. M.; Barros, M. T.; Maycock, C. D. J. Chem. Soc., Perkin Trans. 1 1987, 1221-1223.
16. 4). The product was purified by flash chromatography in the presence of 5% triethylamine. The TMS ethers were oxidized with 1.2 equiv. of oxalyl chloride and 2.4 equiv. of dimethyl sulfoxide at -70°C.
17. Nicolaou, K. C.; Ramphal, J. Y; Petasis, N. A.; Serhan, C. N. Angew. Chem., Int. Ed. Engl. 1991, 30, 1100-1116.
18. Lee, T. H.; Crea, A. E. G.; Gant, V; Spur, B. W.; Marron, B. E.; Nicolaou, K. C.; Reardon, E.; Brezinski, M.; Serhan, C. N. Am. Rev. Resp. Dis. 1990, 141, 1453-1458.
19. Christie, P. E.; Spur, B. W; Lee, T. H. Am. Rev. Respir. Dis, 1992, 145, 1281-1284.
20. Corey, E. J.; Su, W.; Cleaver, M. B. Tetrahedron Lett. 1989, 32, 4181-4184.
21. Nicolaou, K. C.; Zipkin, R. E.; Dolle, R. E.; Harris, B. D. J. Am. Chem. Soc. 1984, 106, 3548-3551.
22. Nakatsuka, M.; Ragan, J. A.; Sammakia, T.; Smith, D. B.; Uehling, D. E.; Schreiber, S. L. J. Am. Chem. Soc. 1990, 112, 5583-5601.
23. 3, 75.5 MHz): δ 204.6, 77.0, 32.7, 31.6, 24.1, 22.4, 13.8, 6.7, 4.7.
24. Mori, Y; Asai, M.; Okumura, A.; Furukawa, H. Tetrahedron 1995, 51, 5299-5314.
25. Furrow, M. E.; Schaus, S. E.; Jacobsen, E. N. J. Org. Chem. 1998, 63, 6776-6777.
26. Leblanc, Y; Fitzsimmons, B. J.; Adams, J.; Perez, F.; Rokach, J. J. Org. Chem. 1986, 51, 789-793.
27. Taffer, I. M.; Zipkin. R. E. Tetrahedron Lett. 1997, 28, 6543-6544.
28. Corey, E. J.; Marfat, A.; Munroe, J. E.; Kim, K. S.; Hopkins, P. B.; Brion, F. Tetrahedron Lett. 1981, 22, 1077-1080.
29. Lee, T. H.; Lympany, P.; Crea, A. E. G.; Spur, B. W. Biochem. Biophys. Res. Commun. 1991, 180, 1416-1421.
30. Yadav, J. S.; Barma, D. K.; Dutta, D. Tetrahedron Lett. 1998, 39, 143-146.
31. Corey, E. J.; Fuchs, P. L. Tetrahedron Lett. 1972. 3769-3772.