A substrate controlled, very highly diastereoselective Morita-Baylis- Hillman reaction: A remote activation of the diastereofacial selectivity in the synthesis of C-3-branched deoxysugars

Tetrahedron

Volumn 60, Issue 50, 2004, Pages 11399-11406

  Sagar, Ram ^a   Pant, Chandra Shekhar ^a   Pathak, Rashmi ^a   Shaw, Arun K ^a  

^a CENTRAL DRUG RESEARCH INSTITUTE   (India)

Author keywords

2,3 Dideoxy sugar derivatives; Diastereoselective; Morita Baylis Hillman reaction

Indexed keywords

ALDEHYDE DERIVATIVE; BENZALDEHYDE DERIVATIVE; DEOXYSUGAR; ISOPROPYL 6 HYDROXY 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O (TRIMETHYLACETYL) 3 (1 HYDROXYDECYL) 2,3 DIDEOXY ALPHA DEXTRO THREO HEX 2 ENOPYRANOSIDE; ISOPROPYL 6 O (TRIMETHYLACETYL) 3 [HYDROXY(2 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO THREO HEX 2 ENOPYRANOSIDE; ISOPROPYL 6 O (TRIMETHYLACETYL) 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO THREO HEX 2 ENOPYRANOSIDE; ISOPROPYL 6 O 4 NITROBENZYL 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O ACETYL 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 (1 HYDROXYBUTYL) 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 (1 HYDROXYDECYL) 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 (HYDROXYPHENYLMETHYL) 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 [HYDROXY(2 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 [HYDROXY(3 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 [HYDROXY(4 FLUOROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLACETYL 3 [HYDROXY(4 TRIFLUOROMETHYLPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLDIMETHYLSILYL 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; ISOPROPYL 6 O TRIMETHYLDIPHENYLSILYL 3 [HYDROXY(4 NITROPHENYL)METHYL] 2,3 DIDEOXY ALPHA DEXTRO GLYCEROHEX 2 ENOPYRANOSID 4 ULOSE; UNCLASSIFIED DRUG;

ARTICLE; BAYLIS HILLMAN REACTION; DRUG SELECTIVITY; DRUG SYNTHESIS; ISOMER; MORITA BAYLIS HILLMAN REACTION; PRIORITY JOURNAL; STEREOCHEMISTRY;

EID: 8744255773     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2004.09.086     Document Type: Article

References (71)

1. Johnson, D. A.; Liu, H.-W. In Comprehensive Natural Products Chemistry; Barton, D., Nakanishi, K., Eds.; Pergamon: Oxford, 1999; Vol. 3, pp 311-365.
2. A.K. Sanki, C.G. Suresh, U.D. Falgune, and T. Pathak Org. Lett. 5 2003 1285 1288
3. H. Feist, K. Peseke, and P. Köll Carbohydr. Res. 247 1993 315 322
4. J. Beyer, P.R. Skaanderup, and R. Madsen J. Am. Chem. Soc. 122 2000 9575 9583
5. Y. Chapleur, and F. Chétien S. Hanessian Preparative Carbohydrate Chemistry 1997 Marcel Dekker New York 207 262
6. J. Yoshimura Adv. Carbohydr. Chem. Biochem. 42 1984 69 134
7. B. Fraser-Reid, C.S. Burgey, and R. Vollerthum Pure Appl. Chem. 70 1998 285 288
8. B. Fraser-Reid Acc. Chem. Res. 29 1996 57 66
9. S. Hanessian Total Synthesis of Natural Products: The 'Chiron' Approach 1983 Pergamon Oxford
10. H. Grisebach, and R. Schmid Angew. Chem., Int. Ed. Engl. 11 1972 159 173
11. A. Gupta, and Y.D. Vankar Tetrahedron 56 2000 8525 8531
12. T.D. Inch Tetrahedron 40 1984 3161 3213
13. J.S. Brimacombe, A.J. Rollins, and S.W. Thompson Carbohydr. Res. 31 1973 108 113
14. A. Calvo-Mateo, M.-J. Camarasa, A. Díaz-Ortíz, F.G.D.L. Heras, and A. Alemany J. Carbohydr. Chem. 8 1989 395 404 and references cited therein
15. O. Moradei, C.M. du Mortier, A.F. Cirelli, and J. Thiem J. Carbohydr. Chem. 18 1999 15 29
16. B. Kuhla, K. Peseke, G. Thiele, and M. Michalik J. Prakt. Chem. 342 2000 240 244
17. T. Müller, and R.R. Schmidt Tetrahedron Lett. 38 1997 5473 5476
18. B.M. Trost I. Fleming Comprehensive Organic Synthesis Vols. 1-9 1991 Pergamon New York
19. R. Roy, R. Dominique, and S.K. Das J. Org. Chem. 64 1999 5408 5412
20. Y. Canac, E. Levoirier, and A. Lubineau J. Org. Chem. 66 2001 3206 3210
21. K. Morita, Z. Suzuki, and H. Hirose Bull. Chem. Soc. Jpn 41 1968 2815 2816
22. (b) Baylis, A. B.; Hillman, M. E. D. German Patent 2155113, 1972; Chem. Abstr. 1972, 77, 34174q.
23. For reviews: (a) D. Basavaiah, A.J. Rao, and T. Satyanarayana Chem. Rev. 103 2003 811 891
24. P. Lānger Angew. Chem., Int. Ed. 39 2000 3049 3052
25. (c) Ciganek, E. In Organic Reactions; Paquette, L. A.; Wiley: New York, 1997; Vol. 51, pp 201-350.
26. D. Basavaiah, P.D. Rao, and R.S. Hyma Tetrahedron 52 1996 8001 8062
27. S.E. Drews, and G.H.P. Roos Tetrahedron 44 1988 4653 4670
28. N.T. McDougal, and S.E. Schaus J. Am. Chem. Soc. 125 2003 12094 12095 and references cited therein
29. D. Balen, and H. Adolfsson Tetrahedron Lett. 44 2003 2521 2524
30. V.K. Aggarwal, A.M.M. Castro, A. Mereu, and H. Adams Tetrahedron Lett. 43 2002 1577 1581
31. M. Shi, and Y.-M. Xu Angew. Chem., Int. Ed. 41 2002 4507 4510
32. B. Alcaide, P. Almendros, and C. Aragoncillo J. Org. Chem. 66 2001 1612 1620
33. K.S. Yang, and K. Chen Org. Lett. 2 2000 729 730
34. (f) For a short review on attempts towards Baylis-Hillman reaction see: P. Lānger Angew. Chem., Int. Ed. 39 2000 3049 3052
35. M.D. Evans, and P.T. Kaye Synth. Commun. 29 1999 2137 2146
36. B. Alcaide, P. Almendros, and C. Aragoncillo Chem. Commun. 1999 1913 1914
37. B. Alcaide, P. Almendros, and C. Aragoncillo Tetrahedron Lett. 40 1999 7537 7540
38. Y. Iwabuchi, M. Nakatani, N. Yokoyama, and S. Hatakeyama J. Am. Chem. Soc. 121 1999 10219 10220
39. J.C. Bussolari, K. Beers, P. Lalan, W.V. Murray, D. Gauthier, and P. McDonnell Chem. Lett. 1998 787 788
40. A.G.M. Barrett, A.S. Cook, and A. Kamimura Chem. Commun. 1998 2533 2534
41. T. Oishi, H. Oguri, and M. Hirama Tetrahedron: Asymmetry 6 1995 1241 1244
42. A. Gilbert, T.W. Heritage, and N.S. Isaacs Tetrahedron: Asymmetry 2 1991 969 972
43. D. Basavaiah, V.V.L. Gowriswari, P.K.S. Sarma, and P.D. Rao Tetrahedron Lett. 31 1990 1621 1624
44. Y. Iwabuchi, M. Furukawa, T. Esumi, and S. Hatakeyama Chem. Commun. 2001 2030 2031
45. L.J. Brzezinski, S. Rafel, and J.W. Leahy J. Am. Chem. Soc. 119 1997 4317 4318
46. Y.-H. Zhu, and P. Vogel Synlett 2001 79 81
47. J. Barbero-J, R. Demange, K. Schenk, and P. Vogel J. Org. Chem. 66 2001 5132 5138
48. Y.-H. Zhu, R. Demange, and P. Vogel Tetrahedron: Asymmetry 11 2000 263 282
49. P.R. Krishna, V. Kannan, G.V.M. Sharma, and M.H.V. Ramana Rao Synlett 2003 888 890
50. P.R. Krishna, V. Kannan, A. Ilangovan, and G.V.M. Sharma Tetrahedron: Asymmetry 12 2001 829 837
51. N. Prévost, and F. Rouessac Synth. Commun. 27 1997 2325 2335
52. G. Li, H.-X. Wei, J.J. Gao, and T.D. Caputo Tetrahedron Lett. 41 2000 1 5
53. M. Taniguchi, T. Hino, and Y. Kishi Tetrahedron Lett. 27 1986 4767 4770
54. G. Li, H.-X. Wei, J.J. Gao, and J. Johnson Synth. Commun. 32 2002 1765 1773
55. Z. Han, S. Uehira, H. Shinokubo, and K. Oshima J. Org. Chem. 66 2001 7854 7857
56. M. Shi, and Y.-S. Feng J. Org. Chem. 66 2001 406 411
57. H.-X. Wei, S.H. Kim, T.D. Caputo, D.W. Purkiss, and G. Li Tetrahedron 56 2000 2397 2401
58. S. Uehira, Z. Han, H. Shinokubo, and K. Oshmia Org. Lett. 1 1999 1383 1385
59. D. Basavaiah, K. Muthukumaran, and B. Sreenivasulu Synlett 1999 1249 1250
60. M. Shi, and J.-K. Jiang Tetrahedron 56 2000 4793 4797
61. T. Bauer, and J. Tarasiuk Tetrahedron: Asymmetry 12 2001 1741 1745
62. S. Kinoshita, H. Kinoshita, T. Iwamura, S.-i. Watanabe, and T. Kataoka Chem. Eur. J. 9 2003 1496 1502 and references cited therein
63. R. Pathak, A.K. Shaw, and A.P. Bhaduri Tetrahedron 58 2002 3535 3541
64. R. Pathak, C.S. Pant, A.K. Shaw, A.P. Bhaduri, A.N. Gaikward, S. Sinha, A. Srivastava, K.K. Srivastava, V. Chaturvedi, R. Srivastava, and B.S. Srivastava Bioorg. Med. Chem. 10 2002 3187 3196
65. T. Amaya, D. Takahashi, H. Tanaka, and T. Takahashi Angew. Chem., Int. Ed. 42 2003 1833 1836
66. H. Kunz, B. Müller, and J. Weissmüller Carbohydr. Res. 171 1987 25 34
67. H.E. Zimmerman, and M.D. Traxler J. Am. Chem. Soc. 79 1957 1920 1923
68. 2AlI at -95 °C→-78 °C.
69. C.R. Harris, S.D. Kuduk, A. Balog, K.A. Savin, and S.J. Danishefsky Tetrahedron Lett. 40 1999 2267 2270
70. R.S. Atkinson Stereoselective Synthesis 1995 Wiley England
71. E.A. Couladouros, and A.T. Strongilos Angew. Chem., Int. Ed. 41 2002 3677 3680