Synthesis of chiral β-iodo-and vinylorganophosphorus(V) compounds by fragmentation of carbohydrate anomeric alkoxyl radicals

Organic Letters

Volumn 15, Issue 2, 2013, Pages 250-253

  Hernández Guerra, Daniel ^a   Rodríguez, María S ^a   Suárez, Ernesto ^a  

^a INSTITUTO DE PRODUCTOS NATURALES Y AGROBIOLOGÍA   (Spain)

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOL DERIVATIVE; ALKOXY RADICAL; AMINO ACID; CARBOHYDRATE; IODINATED HYDROCARBON; ORGANOPHOSPHORUS COMPOUND; SUGAR ALCOHOL; VINYL DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CHEMISTRY; COMBINATORIAL CHEMISTRY; STEREOISOMERISM; SYNTHESIS;

ALCOHOLS; AMINO ACIDS; CARBOHYDRATES; COMBINATORIAL CHEMISTRY TECHNIQUES; HYDROCARBONS, IODINATED; MOLECULAR STRUCTURE; ORGANOPHOSPHORUS COMPOUNDS; STEREOISOMERISM; SUGAR ALCOHOLS; VINYL COMPOUNDS;

EID: 84872570435     PISSN: 15237060     EISSN: 15237052     Source Type: Journal    
DOI: 10.1021/ol302939z     Document Type: Article

References (44)

1. Ananikov, V. P.; Khemchyan, L. L.; Beletskaya, I. P. Synlett 2009, 2375-2381
2. Coudray, L.; Montchamp, J.-L. Eur. J. Org. Chem. 2008, 3601-3613
3. Gaumont, A. C.; Gulea, M. In Science of Synthesis: Houben-Weyl Methods of Molecular Transformations; Molander, G. A., Ed.; Thieme: Stuttgart, 2006; Vol. 33, pp 665-694.
4. Dembitsky, V. M.; Al Quntar, A. A. A.; Haj-Yehia, A.; Srebnik, M. Mini-Rev. Org. Chem. 2005, 2, 91-109
5. Maffei, M. Curr. Org. Chem. 2004, 1, 355-375
6. Wang, H.-Q.; Liu, Z.-J. Chin. J. Org. Chem. 2003, 23, 321-330
7. Minami, T.; Okauchi, T.; Kouno, R. Synthesis 2001, 349-357
8. Minami, T.; Motoyoshiya, J. Synthesis 1992, 333-349
9. Gaumont, A. C.; Gulea, M. In Science of Synthesis, Houben Weyl Methods of Molecular Transformations; Georg Thieme Verlag KG: Stuttgart, 2007; Vol. 33, pp 701-710. Selected representative examples
10. Ortial, S.; Montchamp, J.-L. Org. Lett. 2011, 13, 3134-3147
11. González-Nogal, A. M.; Cuadrado, P.; Sarmentero, M. A. Tetrahedron 2010, 66, 9610-9619
12. Chernysheva, N. A.; Yas'ko, S. V.; Gusarova, N. K.; Trofimov, B. A. Mendeleev Commun. 2010, 20, 20-21
13. Kawaguchi, S.; Nagata, S.; Nomoto, A.; Sonoda, M.; Ogawa, A. J. Org. Chem. 2008, 73, 7928-7933
14. Oliana, M.; King, F.; Horton, P. N.; Hursthouse, M. B.; Hii, K. K. J. Org. Chem. 2006, 71, 2472-2479
15. For a review, see: Palacios, F.; Alonso, C.; de los Santos, J. M. Chem. Rev. 2005, 105, 899-931
16. Shvchenko, V.; Engel, R. Heteroatom. Chem. 1998, 9, 495-502
17. Kiyokawa, K.; Suzuki, I.; Yasuda, M.; Baba, A. Eur. J. Org. Chem. 2011, 2163-2171
18. Hocková, D.; Holy, A.; Masojídkvá, M.; Keough, D. T.; Jersey, J.; Guddat, L. W. Bioorg. Med. Chem. 2009, 17, 6218-6232
19. Balczewski, P.; Pietrzykowski, W. M. Tetrahedron 1997, 53, 7291-7304
20. Lai, C.; Xi, C.; Chen, W.; Hua, R. Tetrahedron 2006, 62, 6295-6302
21. Xi, C.; Ma, M.; Li, X. Chem. Commun. 2001, 2554-2555
22. Takahashi, H.; Inagaki, S.; Yoshii, N.; Gao, F.; Nishihara, Y.; Takagi, K. J. Org. Chem. 2009, 74, 2794-2797
23. de Armas, P.; Francisco, C. G.; Suárez, E. Angew. Chem., Int. Ed. Engl. 1992, 31, 772-774
24. de Armas, P.; Francisco, C. G.; Suárez, E. J. Am. Chem. Soc. 1993, 115, 8865-8866
25. González, C. C.; Kennedy, A. R.; León, E. I.; Riesco-Fagundo, C.; Suárez, E. Angew. Chem., Int. Ed. 2001, 40, 2326-2328
26. Takano, A.; Fukuhara, H.; Ohno, T.; Kutsuma, M.; Fujimoto, T.; Shirai, H.; Iriye, R.; Kakehi, A.; Yamamoto, I. J. Carbohydr. Chem. 2003, 22, 443-457
27. Bolitt, V.; Mioskowski, C.; Lee, S.-G.; Falck, J. R. J. Org. Chem. 1990, 55, 5812-5813
28. Koviach, J. L.; Chappell, M. D.; Halcomb, R. L. J. Org. Chem. 2001, 66, 2318-2326
29. Camps, P.; Cardellach, J.; Font, J.; Ortuño, R. M.; Ponsati, O. Tetrahedron 1982, 38, 2395-2402
30. Yadav, J. S.; Reddy, B. V. S.; Reddy, Ch. S. Tetrahedron Lett. 2004, 45, 4583-4586
31. Enders, D.; Saint-Dizier, A.; Lannou, M.-I.; Lenzen, A. Eur. J. Org. Chem. 2006, 29-49
32. Kofoed, T.; Pedersen, E. B. Nucleosides, Nucleotides and Nucleic Acids 1995, 14, 345-347
33. The C-isostere of 26 and 27 (2-deoxy-2-methylene-d-erythro-pentono-1,4- lactone) has been prepared; see: Porto, R. S.; Coelho, F. Synth. Commun. 2004, 34, 3037-3046 and references cited therein
34. Janecka, A.; Wyrebska, A.; Gach, K.; Fichna, J.; Janecki, T. Drug Discovery Today 2012, 17, 561-572
35. Kitson, R. R. A.; Millemaggi, A.; Taylor, R. J. K. Angew. Chem., Int. Ed. 2009, 48, 9426-9451
36. Collard, J.-N.; Benezra, C. Tetrahedron Lett. 1982, 23, 3725-3728
37. Xu, Y.; Li, Z. Tetrahedron Lett. 1986, 27, 3017-3020
38. Quin, L. D. The Heterocyclic Chemistry of Phosphorus; Wiley-Interscience: New York, 1981; pp 350-353.
39. Wróblewski, A. E. Tetrahedron 1983, 39, 1809-1816
40. Piotrowska, D. G. Tetrahedron: Asymmetry 2008, 19, 279-287
41. Coxon, B. Adv. Carb. Chem. Biochem. 2009, 62, 17-82
42. Wróblewski, A. E.; Konieczko, W. T.; Skoweranda, J.; Bukowska-Strzyzewska, M. J. Crystallogr. Spectrosc. Res. 1991, 21, 581-587
43. Wróblewski, A. E. Phosphorus, Sulfur Silicon Relat. Elem. 1991, 6, 97-117
44. Bergesen, K. Acta Chem. Scand. 1970, 24, 1122-1123