Stereoselective functionalization of dihydropyran-3-ols: Application to the synthesis of enantiopure ethyl deoxymonate B

European Journal of Organic Chemistry

Volumn , Issue 14, 2009, Pages 2312-2322

  De La Pradilla, Roberto Fernández ^a   Lwoff, Nadia ^a   Viso, Alma ^a  

^a INSTITUTO DE QUÍMICA ORGÁNICA GENERAL   (Spain)

Author keywords

Dihydroxylation; Epoxidation; Metathesis; Oxygen heterocycles; Rearrangement

Indexed keywords

EID: 66149124755     PISSN: 1434193X     EISSN: 10990690     Source Type: Journal    
DOI: 10.1002/ejoc.200801133     Document Type: Article

References (17)

1. a) G. Wittig, Acc. Chem. Res. 1974, 7,6-14, b) B. E. Maryan- off, A. B. Reitz, Chem. Rev. 1989, 89, 863-927.
2. M. Taillefer, H. J. Cristau, Top. Curr. Chem. 2003, 229, 41-73.
3. E. Gudrinietse, O. Neiland, G. Vanags, J. Gen. Chem. USSR (Engl. Transl.). 1957, 27, 2777.
4. a) G. F. Koger, in The Chemistry of Functional Groups, Supplement D (Eds.: S. Patai, Z. Rappaport), John Wiley & Sons, 1983, 721-811
5. b) P. J. Stang, V. V. Zhdankin, Chem. Rev. 1996, 96, 1123-1178
6. c) A. Varroglis, The Organic Chemistry of Poly- coordinated Iodine, VCH Publishers, New York, 1992
7. d)N.S. Pirkuliev, V. K. Brel, N. S. Zefirov, Russ. Chem. Rev. 2000, 69, 105-120.
8. R. M. Moriarty, I. Prakash, O. Prakash, W. A. Freeman, J. Am. Chem. Soc. 1984, 106, 6082-6084.
9. V. V. Zhdankin, O. Maydanovych, J. Hershbach, J. Bruno, E. D. Matveeva, N. S. Zefirov, Tetrahedron Lett. 2002, 43, 2359-2361.
10. E. D. Matveeva, T. A. Podrugina, Y. K. Grishin, V. V. Tkachev, V. V. Zhdankin, S. M. Aldoshin, N. S. Zefirov, Zh.Org.Chem. 2003, 39, 536-541.
11. E. D. Matveeva, T. A. Podrugina, A. V. Mironov, N. S. Zefirov, Russ. Chem. Bull. in press.
12. H. Razavi, E. T. Powers, H. E. Purkey, S. L. Adamski-Werner, K. P. Chiang, M. T. A. Dendle, J. W. Kelly, Bioorg. Med. Chem. Lett. 2005, 15, 1075-1078.
13. E. Aguilar, A.I. Meyers, Tetrahedron Lett. 1994, 35, 2477-2480.
14. M. Falorni, G. Dettori, G. Giacomelli, Tetrahedron: Asymmetry 1998, 9, 1419-1426.
15. V. W.-F. Tai, D. Spernadio, E. J. Shelton, J. Litvak, K. Pararajasingham, B. Cebon, J. Lohman, J. Eksterowicz, S. Kantak, P. Sabbatini, S. Brown, J. Zeitz, C. Reed, B. Maske, D. Graupe, A. Estevez, J. Oeh, D. Wong, Y. Ni, P. Sprengeler, R. Yee, C. Magill, A. Neri, S. X. Cai, J. Drewe, L. Qiu, J. Herich, B. Tseng, S. Kasibhatla, J. R. Spencer, Bioorg. Med. Chem. Lett. 2006, 16, 4554-4558.
16. M. C. Burla, M. Camalli, B. Carrozzini, G. Cascarano, C. Gia- covazzo, G. Polidori, R. H. Spagna, J. Appl. Crystallogr. 2003, 36, 1103.
17. V. Petricek, M. Dusek, L. Platinus, Structure Determination Software Programs, Institute of Physics, Praha, Czech. Republic, 2000.