A new and effective route to (±)-botryodiplodin and (±)-epi-botryodiplodin acetates using a halogen atom transfer Ueno-Stork cyclization

Tetrahedron Letters

Volumn 47, Issue 44, 2006, Pages 7759-7762

  De Buyck, Laurent ^a   Forzato, Cristina ^b   Ghelfi, Franco ^c   Mucci, Adele ^c   Nitti, Patrizia ^b   Pagnoni, Ugo M ^c   Parsons, Andrew F ^d   Pitacco, Giuliana ^b   Roncaglia, Fabrizio ^c  

^a GHENT UNIVERSITY   (Belgium)

^b UNIVERSITY OF TRIESTE   (Italy)

^c UNIVERSITY OF MODENA AND REGGIO EMILIA   (Italy)

^d UNIVERSITY OF YORK   (United Kingdom)

Author keywords

Acetals; Cyclization; Halocompounds; Radical reactions; Ueno Stork

Indexed keywords

ACETIC ACID DERIVATIVE; AMINE; COPPER CHLORIDE; HALOGEN; TETRAHYDROFURAN;

ARTICLE; ATOM; CATALYSIS; CYCLIZATION; OXIDATION REDUCTION REACTION;

EID: 33748974620     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.08.121     Document Type: Article

References (39)

1. Motoyama Y., Hanada S., Shimamoto K., and Nagashima H. Tetrahedron 62 (2006) 2779-2788
2. Clark A.J., Geden J.V., and Thom S. J. Org. Chem. 71 (2006) 1471-1479
3. Clark A.J. Chem. Soc. Rev. 31 (2002) 1-11
4. Pintauer T., and Matyjaszewski K. Coord. Chem. Rev. 249 (2005) 1155-1184
5. Salom-Roig X.J., Dénès F., and Renaud P. Synthesis (2004) 1903-1928
6. Kobrakov K.I., and Ivanov A.V. Chem. Heterocycl. Compd. 37 (2001) 529-539
7. Ram R.N., and Charles I. Chem. Commun. (1999) 2267-2268
8. Bellesia F., Danieli C., De Buyck L., Galeazzi R., Ghelfi F., Mucci A., Orena M., Pagnoni U.M., Parsons A.F., and Roncaglia F. Tetrahedron 62 (2006) 746-757
9. De Buyck L., Danieli C., Ghelfi F., Pagnoni U.M., Parsons A.F., Pattarozzi M., and Roncaglia F. Tetrahedron 61 (2005) 2871-2877
10. De Buyck L., Cagnoli R., Ghelfi F., Merighi G., Mucci A., Pagnoni U.M., and Parsons A.F. Synthesis (2004) 1680-1685
11. Cagnoli R., Ghelfi F., Pagnoni U.M., Parsons A.F., and Schenetti L. Tetrahedron 59 (2003) 9951-9960
12. Bellesia F., De Buyck L., Ghelfi F., Pagnoni U.M., Parsons A.F., and Pinetti A. Synthesis (2003) 2173-2178
13. Nenaidenko V.G., Korotchenko V.N., Shastin A.V., Tyurin D.A., and Balenkova E.S. Russ. J. Org. Chem. 40 (2004) 1750-1756
14. Clark A.J., Filik R.P., and Thomas G.H. Tetrahedron Lett. 40 (1999) 4885
15. Fujimoto Y., Kamiya M., Tsunoda H., Ohtsubo K., and Tatsuno T. Chem. Pharm. Bull. 28 (1980) 1062-1066
16. Boysen M., Skouboe P., Frisvad J., and Rossen L. Microbiology 142 (1996) 541-549
17. Nakagawa F., Kodama K., and Naito A. Agric. Biol. Chem. 43 (1979) 1597-1598
18. Sen Gupta R., Chandran R.R., and Divekar P.V. Indian J. Exp. Biol. 4 (1966) 152-153
19. Fuska J., Kuhr I., Nemec P., and Fuskova A. J. Antibiot. 27 (1974) 123-127
20. Fuska J., Proksa B., and Uhrin D. Folia Microbiol. 33 (1988) 238-240 (C.A. 1988, 109, 149154)
21. Fuska, J.; Kuhr, I.; Nemec, P.; Katzer, J. CS 169889 (C.A. 1978, 88, 72988).
22. Fuska J. Antibiotiki (Moscow) 22 (1977) 361-365 (C.A. 1977, 87, 341)
23. Naito, A.; Kotani, K.; Nakagawa, F.; Kodama, K. JP 54086693 1979 (C.A. 1979, 91, 156071).
24. Sakai K., Amemiya S., Inoue K., and Kojima K. Tetrahedron Lett. 20 (1979) 2365-2368
25. McCurry Jr. P.M., and Abe K. J. Am. Chem. Soc. 95 (1973) 5824-5825
26. Daub G.W., Edwards J.P., Okada C.R., Allen J.W., Maxey C.T., Wells M.S., Goldstein A.S., Dibley M.J., Wang C.J., Ostercamp D.P., Chung S., Cunningham P.S., and Berliner M.A. J. Org. Chem. 62 (1997) 1976-1985
27. Kurth M.J., and Yu C.-M. J. Org. Chem. 50 (1985) 1840-1845
28. Wilson S.R., and Myers R.S. J. Org. Chem. 40 (1975) 3309-3311
29. McCurry Jr. P.M., and Abe K. Tetrahedron Lett. 14 (1973) 4103-4106
30. Andrey O., Vidonne A., and Alexakis A. Tetrahedron Lett. 44 (2003) 7901-7904
31. Rehnberg N., and Magnusson G. Acta Chem. Scand. 44 (1990) 377-383
32. Mukaiyama T., Wada M., and Hanna J. Chem. Lett. 10 (1974) 1181-1184
33. Nouguier R., Gastaldi S., Stien D., Bertrand M., Villar F., Andrey O., and Renaud P. Tetrahedron: Asymmetry 14 (2003) 3005-3018
34. Dulcere J.-P., Mihoubi M.N., and Rodriguez J. J. Org. Chem. 58 (1993) 5709-5716
35. Renauld F., Moreau S., Lablanche-Combier A., and Tiffon B. Tetrahedron 41 (1985) 955-962
36. Moulé Y., Renauld F., Darracq N., and Douce C. Carcinogenesis 3 (1982) 211-214
37. Salomon R.G. Chem. Phys. Lipids 134 (2005) 1-20
38. Bruckner R. Advanced Organic Chemistry: Reaction Mechanisms (2002), Harcourt/Academic Press, San Diego Chapter 7, pp 279-281
39. Odinokov V.N., and Tolstikov G.A. Russ. Chem. Rev. 50 (1981) 636-656