Intramolecular aldol cyclization of C-4-ulopyranosyl-2′-oxoalkanes controlled by steric effects. Asymmetric synthesis of substituted 8-oxabicyclo[3.2.1]octanones and -octenones and cyclopentenones

Carbohydrate Research

Volumn 339, Issue 15, 2004, Pages 2475-2485

  Zou, Wei ^a   Shao, Huawu ^a   Wu, Shih Hsiung ^b  

^a NATIONAL RESEARCH COUNCIL CANADA   (Canada)

^b INSTITUTE OF BIOLOGICAL CHEMISTRY   (Taiwan)

Author keywords

Elimination; Aldol reaction; Asymmetric synthesis; Cyclization; Cyclopentenones; Oxabicycles

Indexed keywords

INTRAMOLECULAR ALDOL CYCLIZATION; MOLECULAR FEATURES; RING CONTRACTION;

REACTION KINETICS; SOLUTIONS;

ORGANIC COMPOUNDS;

1 C (2,3,6 TRI O BENZYL ALPHA DEXTRO XYLOHEX 4 ULOPYRANOSYL)PROPAN 2 ONE; 2 BENZYLOXY 5 BENZYLOXYMETHYL 5 HYDROXY 4 (2 OXOPROPYL) 4,5 CYCLOPENT 2 ENONE; 3 BENZYLOXY 1 BENZYLOXYMETHYL 7 HYDROXY 8 OXABICYCLO[3.2.1] 3 OCTEN 2 ONE; ALDEHYDE; ALKANE; C (2,3,6 TRI O BENZYL ALPHA DEXTRO XYLOHEX 4 ULOPYRANOSYL)ACETALDEHYDE; C (2,3,6 TRI O BENZYL BETA DEXTRO XYLOHEX 4 ULOPYRANOSYL)ACETALDEHYDE; CYCLOOCTANE DERIVATIVE; CYCLOPENTANONE DERIVATIVE; KETONE; METHYL GROUP; UNCLASSIFIED DRUG;

ADDITION REACTION; ALDOL REACTION; ARTICLE; CHEMICAL REACTION; CYCLIZATION; PRIORITY JOURNAL; RING OPENING; SUBSTITUTION REACTION; SYNTHESIS;

CARBOHYDRATES; CYCLIZATION; CYCLOOCTANES; CYCLOPENTANES; KETONES;

EID: 5144223729     PISSN: 00086215     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.carres.2004.08.008     Document Type: Article

References (50)

1. S. Hanessian Total Synthesis of Natural Products: The Chiron Approach 1983 Pergamon New York
2. B. Fraser-Reid, and R. Tsang Strategies and Tactics in Organic Synthesis Vol. 2 1989 Academic New York 123
3. R.J. Ferrier, and S. Middleton Chem. Rev. 93 1993 2779 2831
4. P.I. Dalko, and P. Sinaÿ Angew. Chem., Int. Ed. Engl. 38 1999 773 777
5. Z.J. Witczak K. Tatsuta Carbohydrate Synthons in Natural Products Chemistry: Synthesis, Functionalization, and Application 2003 ACS Washington, DC
6. K.W. Hunt, and P.A. Grieco Org. Lett. 3 2001 481 484
7. K.W. Hunt, and P.A. Grieco Org. Lett. 4 2002 245 248
8. J.D. White, and Y. Fukuyama J. Am. Chem. Soc. 101 1979 226 228
9. A.V. Rama Rao, J.S. Yadav, and V. Vidyasagar J. Chem. Soc., Chem. Commun. 1985 55 56
10. M. Lautens, J.T. Colucci, S. Hiebert, N.D. Smith, and G. Bouchain Org. Lett. 4 2002 1879 1882
11. M. Lautens, and R.K. Belter Tetrahedron Lett. 33 1992 2617 2620
12. M. Lautens Synlett 1993 177 185
13. A.V. Costa, L.C.A. Barbosa, A.J. Demuner, and A.A. Silva J. Agric. Food Chem. 47 1999 4807 4814
14. A.J. Demuner, L.C.A. Barbosa, and D.P. Veloso J. Agric. Food Chem. 46 1998 1173 1176
15. F. Lopez, L. Castedo, and J.L. Mascarenas Chem. Eur. J. 8 2002 884 899
16. F. Lopez, L. Castedo, and J.L. Mascarenas Org. Lett. 3 2001 623 625
17. F. Lopez, L. Castedo, and J.L. Mascarenas Org. Lett. 2 2000 1005 1007
18. J. Yin, and L.S. Liebeskind J. Am. Chem. Soc. 121 1999 5811 5812
19. S. Kitagaki, M. Anada, O. Kataoka, K. Matsuno, C. Umeda, N. Watanabe, and S. Hashimoto J. Am. Chem. Soc. 121 1999 1417 1418
20. A. Rumbo, L. Castedo, A. Mourino, and J.L. Mascarenas J. Org. Chem. 58 1993 5585 5586
21. R. Grainger, R.B. Owoare, P. Tisselli, and J.W. Steed J. Org. Chem. 68 2003 7899 7902
22. A. Hosomi, and Y. Tominaga B. Trost I. Fleming L.A. Paquette Comprehensive Organic Synthesis Vol. 5, Chapter 5.1 1991 Pergamon Oxford 593
23. H. Hoffmann Angew. Chem., Int. Ed. Engl. 23 1984 1 19
24. R. Noyori, and Y. Hayakawa Org. React. 29 1983 163 344
25. C.M. Marson, J.H. Pink, D. Hall, M.B. Hursthouse, A. Malik, and C. Smith J. Org. Chem. 68 2003 792 798
26. K. Lee, and J.K. Cha J. Am. Chem. Soc. 123 2001 5590 5591
27. G.L. Carroll, and R.D. Little Org. Lett. 2 2000 2873 2876
28. K. Tanino, K. Onuki, K. Asano, M. Miyashita, T. Nakamura, Y. Takahashi, and I. Kuwajima J. Am. Chem. Soc. 125 2003 1498 1500
29. J.D. Winkler, M.B. Rouse, M.F. Greaney, S.J. Harrison, and Y.T. Jeon J. Am. Chem. Soc. 124 2002 9726 9728
30. H. Tang, N. Yusuff, and J.L. Wood Org. Lett. 3 2001 1563 1566
31. W. Zou, Z. Wang, E. Lacroix, S.-H. Wu, and H. Jennings Carbohydr. Res. 334 2001 223 231
32. H. Shao, Z. Wang, E. Lacroix, S.-H. Wu, H. Jennings, and W. Zou J. Am. Chem. Soc. 124 2002 2130 2131
33. Z. Wang, H. Shao, E. Lacroix, S.-H. Wu, H. Jennings, and W. Zou J. Org. Chem. 68 2003 8097 8105
34. W. Zou, E. Lacroix, Z. Wang, and S.-H. Wu Tetrahedron Lett. 44 2003 4431 4433
35. C.W. Ong, C.M. Chen, and S.S. Juang J. Org. Chem. 59 1994 7915 7916
36. P.J. Garegg, H. Hultberg, and S. Wallin Carbohydr. Res. 108 1982 97 101
37. G.H. Jones, and J.G. Moffatt Methods Carbohydr. Chem. 6 1972 315 322
38. R.M. Pollack Tetrahedron 45 1989 4913 4938
39. M.B. Smith, and J. March March's Advanced Organic Chemistry: Reactions, Mechanisms, and Structure 5th ed. 2001 John Wiley & Sons New York pp 327â€"362
40. J.P. Guthrie, and J. Cossar Can. J. Chem. 64 1986 2470 2474
41. L. Somsák, and R.J. Ferrier Adv. Carbohydr. Chem. Biochem. 49 1991 37 92
42. M. Lautens, K. Fagnou, and S. Hiebert Acc. Chem. Res. 36 2003 48 58
43. M. Lautens, S. Hiebert, and J.-L. Renaud Org. Lett. 2 2000 1971 1973
44. K.-H. Chung, H.G. Lee, I.-Y. Choi, and J.R. Choi J. Org. Chem. 66 2001 5937 5939
45. M. Lautens, P. Chiu, and J.T. Colucci Angew. Chem., Int. Ed. Engl. 32 1993 281 283 Also see Ref. 2
46. M.-H. Filippini, R. Faure, and J. Rodrigues J. Org. Chem. 60 1995 6872 6882
47. L.A. Paquette, Q. Zeng, H.-C. Tsui, and J.N. Johnston J. Org. Chem. 63 1998 8491 8509
48. R.E. Gawley, and J. Aube Principles of Asymmetric Synthesis 1st ed. 1996 Pergamon Oxford
49. S. Caddick, S. Cheung, V.E. Doyle, L.M. Frost, M.G. Soscia, V.M. Delisser, M.R.V. Williams, Z.C. Etheridge, S. Khan, P.B. Hitchcock, G. Pairaudeau, and S. Vile Tetrahedron 57 2001 6295 6303
50. A. Pauk Orbital Interaction Theory of Organic Chemistry 2nd ed. 2001 Wiley-Interscience New York