Synthesis of cyclitols via cyclopropanation/palladium-catalyzed ring opening

Synthesis

Volumn , Issue 19, 2008, Pages 3171-3179

  Shan, Mingde ^a   O'Doherty, George A ^a  

^a WEST VIRGINIA UNIVERSITY   (United States)

Author keywords

Carbasugar; Cyclitol; Cyclopropanol; Pd C hydrogenation; Ring opening

Indexed keywords

ACETONE; ALCOHOLS; KETONES; NEGATIVE IONS; ORGANIC COMPOUNDS; STEREOSELECTIVITY; SYNTHESIS (CHEMICAL);

CARBASUGAR; CYCLITOL; CYCLOPROPANOL; PD/C HYDROGENATION; RING OPENING;

STEREOCHEMISTRY;

5A CARBA ALPHA DEXTRO RHAMNOPYRANOSE; 5A CARBA ALPHA LEVO RHAMNOPYRANOSE; 5A CARBA BETA DEXTRO DIGITOPYRANOSE; CARBASUGAR; CARBOHYDRATE; CYCLITOL; CYCLOHEXANE DERIVATIVE; PALLADIUM; QUINIC ACID; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLOPROPANATION; DIASTEREOISOMER; HYDROGENATION; PROTON NUCLEAR MAGNETIC RESONANCE; RING OPENING; STEREOCHEMISTRY; SYNTHESIS;

EID: 53949094340     PISSN: 00397881     EISSN: None     Source Type: Journal    
DOI: 10.1055/s-2008-1067262     Document Type: Article

References (52)

1. Postema, M. H. D. C-Glycoside Synthesis, 1st ed.; CRC Press: Boca Raton, 1995.
2. Carbohydrate Mimics. Concepts and Methods; Chapleur, Y., Ed.; Wiley-VCH: Weinheim, 1998.
3. For a review on cyclitol chemistry, see: Arjona, O.; Gomez, A. M.; Lopez, C.; Plumet, J. Chem. Rev. 2007, 107, 1919.
4. For synthetic approaches to cyclitol published after ref. 3, see: (a) Ortiz, J. C.; Ozores, L.; Cagide-Fagin, F.; Alonso, R. Chem. Commun. 2006, 4239.
5. (b) Chiara, J. L.; Garcia, A.; Sesmilo, E.; Vacas, T. Org. Lett. 2006, 8, 3935.
6. (c) Chakraborty, C.; Vyavahare, V. P.; Dhavale, D. D. Tetrahedron 2007, 63, 11984.
7. (d) Lysek, R.; Schutz, C.; Favre, S.; O'Sullivan, A. C.; Pillonel, C.; Krulle, T.; Jung, P. M. J.; Clotet-Codina, I.; Este, J.; Vogel, R. Bioorg. Med. Chem. 2006, 14, 6355.
8. (e) Corsaro, A.; Pistara, V.; Catelani, G.; D'Andréa, F.; Adamo, R.; Chiacchio, M. A. Tetrahedron Lett. 2006, 47, 6591.
9. (f) Frigell, J.; Cumpstey, I. Tetrahedron Lett. 2007, 48, 9073.
10. (g) Sardinha, J.; Guieu, S.; Deleuze, A.; Fernandez-Alonso, M. C.; Rauter, A. P.; Sinay, P.; Marrot, J.; Jimenez-Babero, J.; Sollogoub, M. Carbohydr. Res. 2007, 342, 1689.
11. (h) Plumet, J.; Gomez, A. M.; Lopez, J. C. Mini-Rev. Org. Chem. 2007, 4, 201.
12. Zhou, M.; O'Doherty, G. A. Curr. Top. Med. Chem. 2008, 8, 114.
13. An Achmatowicz reaction is the oxidative rearrangement of furyl alcohols to 2-substituted 6-hydroxy-2H-pyran-3(6H)-ones: (a) Achmatowicz, O.; Bielski, R. Carbohydr. Res. 1977, 55, 165.
14. (b) Grapsas, I. K.; Couladouros, E. A.; Georgiadis, M. P. Pol. J. Chem. 1990, 64, 823.
15. For its use in carbohydrate synthesis, see: (c) Harris, J. M.; Keranen, M. D.; O'Doherty, G. A. J. Org. Chem. 1999, 64, 2982.
16. (d) Harris, J. M.; Keranen, M. D.; Nguyen, H.; Young, V. G.; O'Doherty, G. A. Carbohydr. Res. 2000, 328, 17.
17. For examples of oligosaccharides, see: (e) Guo, H.; O'Doherty, G. A. Angew. Chem. Int. Ed. 2007, 46, 5206.
18. (f) Babu, R. S.; Zhou, M.; O'Doherty, G. A. J. Am. Chem. Soc. 2004, 126, 3428.
19. (g) Zhou, M.; O'Doherty, G. A. Org. Lett. 2008, 10, 2283.
20. The application of this approach to carbasugar 1-phosphates has been communicated; the full development of this methodology is reported here, see: Shan, M.; O'Doherty, G. A. Org. Lett. 2008, 10, 3381.
21. (a) Federspiel, M.; Fischer, R.; Hennig, M.; Mair, H.-J.; Oberhauser, T.; Rimmler, G.; Albiez, T.; Bruhin, J.; Estermann, H.; Gandert, C.; Gockel, V.; Gotzo, S.; Hoffmann, U.; Huber, G.; Janatsch, G.; Lauper, S.; Rockel-Stabler, O.; Trussardi, R.; Zwahlen, A. G. Org. Process Res. Dev. 1999, 3, 266.
22. (b) Trost, B. M.; Romero, A. G. J. Org. Chem. 1986, 51, 2332.
23. (c) Audia, J. E.; Boisvert, L.; Patten, A. D.; Villalobos, A.; Danishefsky, S. J. J. Org. Chem. 1989, 54, 3738.
24. (d) Barros, M. T.; Maycock, C. D.; Ventura, M. R. J. Org. Chem. 1997, 62, 3984.
25. Tsuda, T.; Satomi, H.; Hayashi, T.; Saegusa, T. J. Org. Chem. 1987, 52, 439.
26. (a) Lipshutz, B. H.; Chrisman, W.; Noson, K.; Papa, P.; Sclafani, J. A.; Vivian, R. W.; Keith, J. M. Tetrahedron 2000, 56, 2779.
27. (b) Mahoney, W. S.; Stryker, J. M. J. Am. Chem. Soc. 1989, 111, 8818.
28. For a recent review, see: Kulinkovich, O. G. Chem. Rev. 2003, 103, 2597.
29. (a) Ojima, I.; Kogure, T. Organometallics 1982, 1, 1390.
30. (b) Tojo, S.; Isobe, M. Synthesis 2005, 1237.
31. For a review on Simmons-Smith cyclopropanation, see: (a) Hoveyda, A. H.; Evans, D. A.; Fu, G. C. Chem. Rev. 1993, 93, 1307.
32. (b) Lautens, M.; Klute, W.; Tam, W. Chem. Rev. 1996, 96, 49.
33. (c) Lebel, H.; Marcoux, J.-F.; Molinaro, C.; Charette, A. B. Chem. Rev. 2003, 103, 977.
34. For acid and base opening, see ref. 11. For examples of acid-catalyzed opening, see: (a) Schreiber, S. L.; Smith, D. B.; Schulte, G. J. Org. Chem. 1989, 54, 5994.
35. (b) Paquette, L. A.; Ross, R. J.; Shi, Y. J. J. Org. Chem. 1990, 55, 1589.
36. For examples of base-catalyzed opening, see: (c) Barnier, J. P.; Blanco, L.; Rousseau, G.; Guibe-Jampel, E.; Fresse, I. J. Org. Chem. 1993, 58, 1570.
37. Park, S.-B.; Cha, J. K. Org. Lett. 2000, 2, 147.
38. Tarros, M. T.; Maycock, C. D.; Ventura, M. R. J. Org. Chem. 1997, 62, 3984.
39. For examples of the trapping of organometallic intermediates with hydrogen, see: (a) Ngai, M.-Y.; Kong, J.-R.; Krische, M. J. J. Org. Chem. 2007, 72, 1063.
40. (b) Iida, H.; Krische, M. J. Top. Curr. Chem. 2007, 279, 77.
41. (c) Skucas, E.; Ngai, M.-Y.; Komanduri, V.; Krische, M. J. Acc. Chem. Res. 2007, 40, 1394.
42. VanRheenen, V.; Kelly, R. C.; Cha, D. Y. Tetrahedron Lett. 1976, 17, 1973.
43. (a) Montchamp, J.-L.; Tian, F.; Hart, M. E.; Frost, J. W. J. Org. Chem. 1996, 61, 3897.
44. (b) Barros, M. T.; Maycock, C. D.; Ventura, M. R. J. Chem. Soc., Perkin Trans. 1 2001, 166.
45. (a) Myers, A. G.; Zheng, B. J. Am. Chem. Soc. 1996, 118, 4492.
46. (b) Myers, A. G.; Zheng, B. Tetrahedron Lett. 1996, 37, 4841.
47. (c) Myers, A. G.; Zheng, B.; Movassaghi, M. J. Org. Chem. 1997, 62, 7507.
48. (d) Haukaas, M. H.; O'Doherty, G. A. Org. Lett. 2002, 4, 1771.
49. (e) Zhou, M.; O'Doherty, G. A. Org. Lett. 2006, 8, 4339.
50. (a) Mitsunobu, O.; Yamada, Y. Bull. Chem. Soc. Jpn. 1967, 40, 2380.
51. (b) Mitsunobu, O. Synthesis 1981, 1.
52. The optical rotations of compounds 7 and ent-7 prepared by us were significantly higher than reported; however, the remaining spectral data for compound 7 and ent-7 matched those of the reported data for ent-7 prepared by Redlich et al., see: Redlich, H.; Sudau, W.; Szadenings, A. K.; Vollerthun, R. Carbohydr. Res. 1992, 226, 57.