Synthesis of 4-membered carbasugars by way of stereoselective SmI 2-mediated aldehyde-alkene cyclization

Journal of Organic Chemistry

Volumn 78, Issue 13, 2013, Pages 6751-6757

  Nocquet, Pierre Antoine ^a   Hazelard, Damien ^a   Gruntz, Guillaume ^a   Compain, Philippe ^a,b  

^a UNIVERSITÉ DE STRASBOURG   (France)

^b INSTITUT UNIVERSITAIRE DE FRANCE   (France)

Author keywords

[No Author keywords available]

Indexed keywords

HYDROCARBONS;

CARBASUGARS; STEREO-SELECTIVE; STEREOCONTROL; STEREODIVERGENT SYNTHESIS; VITAMIN C;

ALDEHYDES;

ALDEHYDE; ALKENE; ASCORBIC ACID; CARBASUGAR; OXAZIRIDINE DERIVATIVE;

ARTICLE; CHEMICAL STRUCTURE; CYCLIZATION; DIASTEREOISOMER; HYDROGENOLYSIS; OXIDATION; REACTION TIME; REDUCTION; STATIC ELECTRICITY; STEREOCHEMISTRY; SWERN OXIDATION; SYNTHESIS; CHEMISTRY; CONFORMATION; STEREOISOMERISM;

ALDEHYDES; ALKENES; CARBASUGARS; CYCLIZATION; MOLECULAR CONFORMATION; STEREOISOMERISM;

EID: 84880008399     PISSN: 00223263     EISSN: 15206904     Source Type: Journal    
DOI: 10.1021/jo400732a     Document Type: Article

References (50)

1. Sears, P.; Wong, C.-H. Angew. Chem., Int. Ed. 1999, 38, 2300-2324
2. Compain, P.; Martin, O. R. Bioorg. Med. Chem. 2001, 9, 3077-3092
3. Ernst, B.; Magnani, J. L. Nat. Rev. Drug Discovery 2009, 8, 661-677
4. Koester, D. C.; Holkenbrink, A.; Werz, D. B. Synthesis 2010, 3217-3242
5. Chapleur, Y. Carbohydrate Mimics, Concepts and Methods; Wiley-VCH: Weinheim, 1998.
6. McCasland, G. E.; Furuta, S.; Durham, L. J. J. Org. Chem. 1966, 31, 1516-1521
7. Suami, T.; Ogawa, S. Adv. Carbohydr. Chem. Biochem. 1990, 48, 21-90
8. Ogawa, S. In Carbohydrate Mimics, Concepts and Methods; Wiley-VCH: Weinheim, 1998; pp 87-106.
9. Arjona, O.; Gomez, A. M.; Cristobal Lopez, J.; Plumet, J. Chem. Rev. 2007, 107, 1919-2036
10. Ogawa, S.; Kanto, M.; Suzuki, Y. Mini-Rev. Med. Chem. 2007, 7, 679-691
11. Chen, X.; Fan, Y.; Zheng, Y.; Shen, Y. Chem. Rev. 2003, 103, 1955-1978
12. Mahmud, T. Nat. Prod. Rep. 2003, 20, 137-166
13. Crimmins, M. T. Tetrahedron 1998, 54, 9229-9272
14. Berecibar, A.; Grandjean, C.; Siriwardena, A. Chem. Rev. 1999, 99, 779-844
15. Schiffelers, R.; Storm, G.; Bakker-Woudenberg, I. J. Antimicrob. Chemother. 2001, 48, 333-344
16. Mingeot-Leclercq, M.-P.; Glupczynski, Y.; Tulkens, P. M. Antimicrob. Agents Chemother. 1999, 43, 727-737
17. Chiasson, J. L.; Josse, R. G.; Gomis, R.; Hanefeld, M.; Karasik, A.; Laakso, M. Lancet 2002, 359, 2072-2077
18. Chen, X.; Zheng, Y.; Shen, Y. Curr. Med. Chem. 2006, 13, 109-116
19. Ramana, C. V.; Chaudhuri, S. R.; Gurjar, M. K. Synthesis 2007, 523-528
20. Rassu, G.; Auzzas, L.; Pinna, L.; Zambrano, V.; Zanardi, F.; Battistini, L.; Gaetani, E.; Curti, C.; Casiraghi, G. J. Org. Chem. 2003, 68, 5881-5885
21. Sisu, E.; Sollogoub, M.; Mallet, J.-M.; Sinaÿ, P. Tetrahedron 2002, 58, 10189-10196
22. Marco-Contelles, J.; De Opazo, E. J. Carbohydr. Chem. 2002, 21, 201-218
23. Marco-Contelles, J.; De Opazo, E. Tetrahedron Lett. 1999, 40, 4445-4448
24. Paquette, L. A.; Moura-Letts, G.; Wang, G. P. J. Org. Chem. 2009, 74, 2099-2107
25. Paquette, L. A.; Zhang, Y. J. Org. Chem. 2006, 71, 4353-4363
26. Mehta, G.; Pallavi, K. Chem. Commun. 2002, 2828-2829
27. Wang, W.; Zhang, Y.; Zhou, H.; Blériot, Y.; Sinaÿ, P. Eur. J. Org. Chem. 2001, 1053-1059
28. Wang, W.; Zhang, Y.; Sollogoub, M.; Sinaÿ, P. Angew. Chem., Int. Ed. Engl. 2000, 39, 2466-2467
29. Mehta, G.; Pallavi, K.; Katukojvala, S. Tetrahedron Lett. 2009, 50, 4519-4522
30. Compain, P.; Decroocq, C.; Iehl, J.; Holler, M.; Hazelard, D.; Mena Barragán, T.; Ortiz Mellet, C.; Nierengarten, J.-F. Angew. Chem., Int. Ed. 2010, 49, 5753-5756
31. Chagnault, V.; Compain, P.; Lewinski, K.; Ikeda, K.; Asano, N.; Martin, O. R. J. Org. Chem. 2009, 74, 3179-3182
32. For examples of sugar oxetanoses, see: Nishiyama, S.; Ohgiya, T.; Yamamura, S.; Kato, K.; Nagai, M.; Takita, T. Tetrahedron Lett. 1990, 31, 705-708
33. For examples of cyclobutyl nucleosides, see: Norbeck, D. W.; Kern, E.; Hayashi, S.; Rosenbrook, W; Sham, H.; Herrin, T.; Plattner, J. J.; Erickson, J.; Clement, J.; Swanson, R.; Shipkowitz, N.; Hardy, D.; Marsh, K.; Arnett, G.; Shannon, W.; Broder, S.; Mitsuya, H. J. Med. Chem. 1990, 33, 1281-1285
34. 2-mediated carbonyl-alkene coupling for the synthesis of small carbocyclic rings, see: Harb, H. Y.; Procter, D. J. Synlett 2012, 6-20
35. Williams, D. B. G.; Blann, K. Eur. J. Org. Chem. 2004, 3286-3291
36. Williams, D. B. G.; Caddy, J.; Blann, K.; Grové, J. J. C.; Holzapfel, C. W. Synthesis 2009, 2009-2014
37. Schöning, K.-U; Scholz, P.; Wu, X.; Guntha, S.; Delgado, G.; Krishnamurthy, R.; Eschenmoser, A. Helv. Chim. Acta 2002, 85, 4111-4153
38. Spectroscopic and analytical data of lactone 7 are in good agreement with literature values, see: Pabba, J.; Rempel, B. P.; Withers, S. G.; Vasella, A. Helv. Chim. Acta 2006, 89, 635-666
39. Vu, N. Q.; Chai, C. L. L.; Lim, K. P.; Chia, S. C.; Chen, A. Tetrahedron 2007, 63, 7053-7058
40. Weinges, K.; Schmidbauer, S. B.; Schick, H. Chem. Ber. 1994, 127, 1305-1309
41. Molander, G. A.; McKie, J. A. J. Org. Chem. 1992, 57, 3132-3139
42. Sadasivam, D. V.; Antharjanam, P. K. S.; Prasad, E.; Flowers, R. A., II J. Am. Chem. Soc. 2008, 130, 7228-7229
43. Johnston, D.; McCusker, C. M.; Procter, D. J. Tetrahedron Lett. 1999, 40, 4913-4916
44. Chopade, P. R.; Prasad, E.; Flowers, R. A. J. Am. Chem. Soc. 2004, 126, 44-45
45. Edmonds, D. J.; Muir, K. W.; Procter, D. J. J. Org. Chem. 2003, 68, 3190-3198
46. Nicolaou, K. C.; Li, A.; Edmonds, D. J.; Tria, G. S.; Ellery, S. P. J. Am. Chem. Soc. 2009, 131, 16905-16918
47. Gilles, P.; Py, S. Org. Lett. 2012, 14, 1042-1045
48. Grieco, P. A.; Gilman, S.; Nishizawa, M. J. Org. Chem. 1976, 41, 1485-1486
49. For the preparation of Davis oxaziridine, see: Vishwakarma, L. C.; Stringer, O. D.; Davis, F. A. Org. Synth. 1988, 66, 203-210
50. Buchotte, M.; Muzard, M.; Plantier-Royon, R. Eur. J. Org. Chem. 2008, 3529-3534