Stereoselective synthesis of versatile 2-chloromercurium-3,5-syn-dihydroxy esters via intramolecular oxymercuration

Tetrahedron

Volumn 64, Issue 37, 2008, Pages 8766-8772

  Bonini, Carlo ^a   Campaniello, Maria ^a   Chiummiento, Lucia ^a   Videtta, Valeria ^a  

^a UNIVERSITY OF BASILICATA   (Italy)

Author keywords

1,3 syn Diol; Demercuration; Lactonization; Oxymercuration

Indexed keywords

ACETONE; ALCOHOL; ESTER DERIVATIVE; LACTONE DERIVATIVE;

ARTICLE; CHEMICAL MODIFICATION; CHEMICAL REACTION; HALOGENATION; HYDROLYSIS; OXYMERCURATION; PRIORITY JOURNAL; STEREOCHEMISTRY; SYNTHESIS;

EID: 48049092006     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.06.094     Document Type: Article

References (52)

1. Nakata T. In: Omura S. (Ed). Macrolide Antibiotics. Chemistry, Biology, and Practice. 2nd ed. (2002), Academic Press, San Diego 181-284
2. Schenider C. Angew. Chem., Int. Ed. 37 (1998) 1375-1378
3. Hoffmann R.W. Angew. Chem., Int. Ed. 42 (2003) 1096-1109
4. Bode S.E., Wolberg M., and Muller M. Synthesis (2006) 557-588
5. Bonini C., Racioppi R., Righi G., and Viggiani L. J. Org. Chem. 58 (1993) 802-803
6. Bonini C., Chiummiento L., and Funicello M. Tetrahedron: Asymmetry 12 (2001) 2755-2760
7. Bonini C., Chiummiento L., Martuscelli A., and Viggiani L. Tetrahedron Lett. 95 (2004) 2177-2179
8. Bonini B., Chiummiento L., Pullez M., Solladié G., and Colobert F. J. Org. Chem. 69 (2004) 5015-5022
9. Overman L.E., and Campbell C.B. J. Org. Chem. 39 (1974) 1474-1481
10. Dreher S.D., Hornberger K.R., Sarraf S.T., and Leighton J.L. Org. Lett. 2 (2000) 3197-3199
11. Evans D.A., and Gauchet-Prunet J.A. J. Org. Chem. 58 (1993) 2446-2453
12. Evans D.A., and Connell B.T. J. Am. Chem. Soc. 125 (2003) 10899-10905
13. Wiseman J.M., McDonald F., and Liotta D.C. Org. Lett. 7 (2005) 3155-3157
14. Bloodworth A.J., and Bunce R.J. J. Chem. Soc. C (1971) 1453-1458
15. Bloodworth A.J., and Griffin I.M. J. Chem. Soc., Perkin Trans. 1 (1974) 688-695
16. Cabaleiro M.C., Ayala A.D., and Johnson M.D. J. Chem. Soc., Perkin Trans. 2 (1973) 1207-1212
17. Gouzoules F.H., and Whitney R.A. J. Org. Chem. 51 (1986) 2024-2030
18. Larock R.C. Solvomercuration/Demercuration in Organic Synthesis (1986), Springer, Berlin
19. Barluenga J., and Yus M. Chem. Rev. 88 (1988) 487-509
20. Kocovsky P., Dunn V., Gogoll A., and Langer V. J. Org. Chem. 64 (1999) 101-119
21. Russell G.A., and Kulkarni S.V. J. Org. Chem. 58 (1993) 2678-2685
22. Raghavan S., Tony K.A., and Reddy S.R. Tetrahedron Lett. 42 (2001) 8383-8386
23. Lukkarila J.L., Hamer G.K., and Georges M.K. Tetrahedron Lett. 45 (2004) 5317-5319
24. We have prepared racemic compounds 5, but several methodologies could be used to obtain optically pure compounds.
25. Bonini C., Chiummiento L., Lopardo M.T., Pullez M., Colobert F., and Solladié G. Tetrahedron Lett. 44 (2003) 2695-2697
26. Nicolaou K.C., Bulger P.G., and Sarlah D. Angew. Chem., Int. Ed. 44 (2005) 4490-4527
27. De Weghe P.V., Eustache J., and Cossy J. Curr. Top. Med. Chem. 5 (2005) 1461-1472
28. Schmidt B., and Hermanns J. Top. Organomet. Chem. 13 (2004) 223-267
29. Fürstner A. Angew. Chem., Int. Ed. 39 (2000) 3012-3043
30. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413-4450
31. 2 was used.
32. 3N (5% v/v) in the eluent prior to chromatography.
33. 2C in the corresponding acetonides. Rychnovsky S.D., Rogers B., and Yang G. J. Org. Chem. 58 (1993) 3511-3515
34. Brown H.C., and Geoghegan Jr. P.J. J. Org. Chem. 35 (1970) 1844-1850
35. Griffith R.C., Gentile R.J., Davidson T.A., and Scott F.L. J. Org. Chem. 44 (1979) 3580-3583
36. Thanavaro A., and Spilling C.D. Phosphorus, Sulfur Silicon Relat. Elem. 177 (2002) 1583-1586
37. The unique example of deprotection of acetonide is reported for 1,2-diol in:. Batovska D.I., Kishimoto T., Bankova V.S., Kamenarska Z.G., and Ubukata M. Molecules 10 (2005) 552-558
38. Guo Z., Chen Y., Goswami A., Hanson R.L., and Patel R.N. Tetrahedron: Asymmetry 17 (2006) 1589-1602
39. Aggarwal V.K., Bae I., and Lee H.-Y. Tetrahedron 60 (2004) 9725-9733
40. Lautens M., Ma S., and Yee A. Tetrahedron Lett. 24 (1995) 4185-4188
41. Takano S., Sugihara Y., and Ogasawara K. Tetrahedron: Asymmetry 4 (1993) 1795-1798
42. Bonini C., Pucci P., Racioppi R., and Viggiani L. Tetrahedron: Asymmetry 3 (1992) 29-32
43. Reformatsky S. Ber. Dtsch. Chem. Ges. 20 (1887) 1210-1211
44. For a review, see:
45. Babu S.A., Yasuda M., Shibata I., and Baba A. J. Org. Chem. 70 (2005) 10408-10419 and references therein
46. Babu S.A., Yasuda M., Okabe Y., Shibata I., and Baba A. Org. Lett. 8 (2006) 3029-3032
47. Nixon J.R., Cudd M.A., and Porter N.A. J. Org. Chem. 43 (1978) 4048-4052
48. 1H NMR spectra, bidimensional analyses (COSY, ghsqc) were made on it.
49. In order to transform the organomercurial compound 2a into the corresponding structurally rigid lactone, hydrolyses of the ketal were made with 5% HCl solution in THF and with AcOH in THF producing the starting α,β-unsaturated ester 5a. However, the acid condition led to product 5a during the purification by column chromatography on silica gel of 2a.
50. Paquette L.A., Bolin D.G., Stepanian M., Branan B.M., Mallavadhani U.V., Tae J., Eisenberg S.W.E., and Rogers R.D. J. Am. Chem. Soc. 120 (1998) 11603-11615
51. Piccinini P., Vidari G., and Zanoni G. J. Am. Chem. Soc. 126 (2004) 5088-5089
52. Compounds 5a-f and 1a-e are known products and they showed the same spectroscopic characteristics reported in the literature.