A simple and stereodivergent strategy for the synthesis of 3′-C-branched 2′,3′-dideoxynucleosides exploiting (Z)-but-2-en-1,4-diol and (R)-2,3-cyclohexylideneglyceraldehyde

Tetrahedron Letters

Volumn 47, Issue 27, 2006, Pages 4701-4705

  Chattopadhyay, Angshuman ^a   Goswami, Dibakar ^a   Dhotare, Bhaskar ^a  

^a BHABHA ATOMIC RESEARCH CENTRE   (India)

Author keywords

(R) 2,3 Cyclohexylideneglyceraldehyde; (Z) But 2 en 1,4 diol; 3 C Branched 2 ,3 dideoxynucleosides; Bimetal redox strategy; Convergent; Crotylation; Oxidation potential (E0); Stereodiversity

Indexed keywords

2',3' DIDEOXYNUCLEOSIDE DERIVATIVE; 2,3 CYCLOHEXYLIDENEGLYCERALDEHYDE; ALCOHOL DERIVATIVE; BROMINE DERIVATIVE; BUT 2 EN 1,4 DIOL; COBALT; COPPER; GLYCERALDEHYDE; IRON; TETRAHYDROFURAN; UNCLASSIFIED DRUG; ZINC;

ADDITION REACTION; ARTICLE; DRUG STRUCTURE; DRUG SYNTHESIS; OXIDATION REDUCTION REACTION;

EID: 33744512132     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2006.04.120     Document Type: Article

References (60)

1. Huryn D.M., and Okabe M. Chem. Rev. 92 (1992) 1745-1768 and references cited therein
2. Duelhom K.L., and Pedersen E.B. Synthesis (1992) 1-22 and references cited therein
3. Wilson L.J., Hager M.W., El-Kattan Y.A., and Liotta D.C. Synthesis (1992) 1465-1479 and references cited therein
4. Yokoyama M., and Momotake A. Synthesis (1999) 1541-1554
5. Yokoyama M. Synthesis (2000) 1637-1655
6. Ludel O.R., and Meier C. Synthesis (2003) 2101-2109
7. Shuto S., Kanazaki M., Ichikawa S., Minakawa N., and Matsuda A. J. Org. Chem. 63 (1998) 746-754 and references cited therein
8. Harry-Okuru R.E., Smith J.M., and Wolfe M.S. J. Org. Chem. 62 (1997) 1754-1789 and references cited therein
9. Ton-That T. Nucleosides Nucleotides 18 (1999) 731-732
10. Takatori S., and Kanda H. J. Med. Chem. 42 (1999) 2901-2908
11. Ichikawa S., Shuto S., Minakawa N., and Matsuda A. J. Org. Chem. 62 (1997) 1368-1375
12. Garg N., Plavec J., and Chattopadhyaya J. Tetrahedron 49 (1993) 5189-5202
13. Ogawa A., Tanaka M., Sasaki T., and Matsuda A. J. Med. Chem. 41 (1998) 5094-5107
14. Vanheusden V., Munier-Lehman H., Froeyen M., Dugue L., Heyerick A., De Keukeleire D., Pochet S., Busson R., Herdewijn P., and Van Calenbergh S. J. Med. Chem. 46 (2003) 3811-3821
15. Uhlmann E., and Peyman A. Chem. Rev. 90 (1990) 543-584
16. Mesmaekar A.D., Haner R., Martin P., and Moser E.H. Acc. Chem. Res. 28 (1995) 366-374
17. Kurreck J., Wyszko E., Clemens G., and Erdmann V.A. Nucleic Acids Res. 30 (2002) 1911-1918
18. Stein C.A. J. Clin. Invest. 108 (2001) 641-644
19. Crooke S.T. Methods Enzymol. 313 (2000) 3-45
20. Heinemann U., Rudolph L.N., Alings C., Morr M., Heikens W., Frank R., and Blocker H. Nucleic Acids Res. 19 (1991) 427-433
21. Svansson L., and Kvarnstrom I. J. Org. Chem. 56 (1991) 2993-2997 and references cited therein
22. Hossain N., Plavec J., and Chattopadhyay J. Tetrahedron 50 (1994) 4167-4178
23. Aguste S.P., and Young D.W. J. Chem. Soc., Perkin Trans. 1 (1995) 395-404
24. Herradon B. Tetrahedron: Asymmetry 2 (1991) 191-194
25. Robins M.J., Doboszewski B., Timoshchuk V.A., and Peterson M.A. J. Org. Chem. 65 (2000) 2939-2945
26. Nomura M., Sato T., Washinosu M., Tanaka M., Shuto S., and Matsuda S. Tetrahedron 58 (2002) 1279-1288
27. Vorbruggen H. Acc. Chem. Res. 28 (1995) 509-520
28. Martin P. Helv. Chim. Acta 79 (1996) 1930
29. Saneyoshi M., and Satoh E. Chem. Pharm. Bull. 27 (1979) 2518-2521
30. Mukaiyama T., Ishikawa T., and Uchino H. Chem. Lett. (1997) 389
31. Vorbruggen H., Krolikiewicz K., and Bennua B. Chem. Ber. 114 (1981) 1234-1255
32. Chattopadhyay A., and Mamdapur V.R. J. Org. Chem. 59 (1995) 585-587
33. Chattopadhyay A., and Dhotare B. Tetrahedron: Asymmetry 9 (1998) 2715-2723
34. Petrier C., and Luche J.L. J. Org. Chem. 50 (1985) 910-912
35. Einhorn C., and Luche J.L. J. Organomet. Chem. 322 (1987) 177
36. Petrier C., Einhorn J., and Luche J.L. Tetrahedron Lett. 26 (1985) 1449-1452
37. 4Si: C, 72.46; H, 8.39. Found, C, 72.29; H, 8.64.
38. 4Si: C, 72.46; H, 8.39. Found, C, 72.69; H, 8.61.
39. 3 (4.9 g, 0.03 mol)] in THF (70 mL) was added Zn dust ( 2.25 g, 0.035 mol for Co and Cu; 1.95 g, 0.03 mol for Fe) in portions over a period of 15 min. The mixture was stirred at ambient temperature for the period as shown in Table 1. The reaction mixture was then treated successively with water (50 mL) and EtOAc (100 mL), stirred for 10 min more and then filtered. The filtrate was treated with 2% aqueous HCl to dissolve a small amount of suspended particles. The organic layer was separated. The aqueous layer was extracted with EtOAc. The combined organic layer was washed with water, brine and then dried. Solvent removal and column chromatography of the residue (silica gel, 0-15% EtOAc in petroleum ether) afforded 5a/5b as an inseparable mixture, and 5c and 5d in pure form.
40. The partial (Co and Cu) to good (Fe) solubility of the metal salts in distilled THF which always contains some moisture, plays a role in facilitating bimetal redox reactions and subsequent crotylation. It has been observed, that in anhydrous THF no crotylation reaction took place presumably due to the very poor solubility of these metal salts.
41. Dhotare B., Salaskar A., and Chattopadhyay A. Synthesis (2003) 2571-2575
42. Dhotare B., and Chattopadhyay A. Tetrahedron Lett. 46 (2005) 3103-3105
43. 4Si: C, 72.46; H, 8.39. Found, C, 72.24; H, 8.11.
44. 4Si: C, 72.46; H, 8.39. Found, C, 72.68; H, 8.30.
45. Marshall J.A., and Garofalo A.W. J. Org. Chem. 58 (1993) 3675-3680
46. 2: C, 72.74; H, 6.78. Found, C, 72.96; H, 7.01.
47. Cherest M., and Felkin H. Tetrahedron Lett. (1968) 2205
48. Anh N.T. Top. Curr. Chem. 88 (1980) 145-170
49. Lane C.F. J. Org. Chem. 39 (1974) 1437-1438
50. Corey E.J., and Suggs J.W. Tetrahedron Lett. (1975) 2647-2650
51. 6Si: C, 69.11; H, 7.86. Found, C, 69.29; H, 8.04.
52. 6Si: C, 67.52; H, 7.33; N, 4.63. Found, C, 67.35; H, 7.54; N, 4.77.
53. Yamamoto Y., and Asao N. Chem. Rev. 93 (1993) 2207-2293 and references cited therein
54. Thomas E.J. Chem. Commun. (1997) 411-418 and references cited therein
55. Denmark S.E., and Fu J. Chem. Rev. 103 (2003) 2763-2793 and references cited therein
56. Hoffmann R.W. Angew. Chem., Int. Ed. Engl. 21 (1982) 555 and references cited therein
57. Roush W.R., and Halterman P.L. J. Am. Chem. Soc. 108 (1986) 294-296
58. Buse C.T., and Heathcock C.H. Tetrahedron Lett. 19 (1978) 1685-1688
59. Marshall J.A. Chem. Rev. 96 (1996) 31-47
60. Kennedy J.W.J., and Hall D.G. Angew. Chem. Int. Ed. 42 (2003) 4732-4739