Diasterodivergent synthesis of optically pure vinyl episulfides and β-hydroxy thiocyanates from a bacterial metabolite

Tetrahedron Letters

Volumn 48, Issue 17, 2007, Pages 3047-3051

  Bellomo, Ana ^a   Gonzalez, David ^a  

^a UNIVERSIDAD DE LA REPÚBLICA   (Uruguay)

Author keywords

[No Author keywords available]

Indexed keywords

BROMOBENZENE; SULFIDE; THIOCYANIC ACID DERIVATIVE;

ARTICLE; EPOXIDATION; RING CLOSING METATHESIS; SYNTHESIS;

BACTERIA (MICROORGANISMS);

EID: 33947582664     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.02.113     Document Type: Article

References (56)

1. Iranpoor N., Firouzabai H., Chitsazi M., and Jafari A.A. Tetrahedron 58 (2002) 7037
2. Dittmer D.C. In: Katritzky A.R., and Rees C.W. (Eds). Thiiranes and Thiirenes in Comprehensive Heterocycle Chemistry Vol. 7 (1984), Pergamon, Elmsfor, NY 132
3. Vedejs E., and Krafft G.A. Tetrahedron 38 (1982) 2857
4. Reynolds D.D., and Fields D.L. Heterocyclic Compounds with Three- and Four-Membered Rings (1964), Interscience, New York 576
5. Vedejs E., and Krafft G.A. Tetrahedron 38 (1982) 2857
6. Ettinger M.G. J. Am. Chem. Soc. 72 (1950) 4792
7. Sander M. Chem. Rev. 66 (1966) 297
8. Doyle F.P., Holland D.O., Hunter W.H., Mayer J.H.C., and Queen A. J. Chem. Soc. (1960) 2665
9. Bouda H., Borredon M.E., Delmas M., and Gaset A. Synth. Commun. 19 (1989) 491 and the references cited therein
10. Chan T.R., and Finkenbine J.R. J. Am. Chem. Soc. 94 (1972) 2880
11. Calo V., Lopez L., Marchese L., and Pesce G. J. Chem. Soc., Chem. Commun. (1975) 621
12. Takido T., Kobayashi Y., and Itabashi K. Synthesis (1986) 779
13. Brimeyer M.O., Mehrota A., Quici S., Nigam A., and Regen S.L. J. Org. Chem. 45 (1980) 4254
14. Bouda H., Borredon M.E., Delmas M., and Gaset A. Synth. Commun. 17 (1987) 943
15. Yadav J.S., Reddy B.V.S., and Baishya G. Synlett (2003) 396
16. Tamami B., and Kiasat A.R. Synth. Commun. 26 (1996) 3953
17. Tamami B., and Kolahdoozan M. Tetrahedron Lett. 45 (2004) 1535
18. Kabboudin B., and Norouzi H. Tetrahedron Lett. 45 (2004) 1283
19. Yadav J.S., Redy B.V.S., Reddy C.S., and Rajasekhar K. J. Org. Chem. 68 (2003) 2525
20. Iranpoor N., and Kazemi F. Synthesis (1996) 821
21. Iranpoor N., and Kazemi F. Tetrahedron 53 (1997) 11377
22. Mohammadpoor-Baltork I., and Alian H. Synth. Commun. 28 (1998) 3943
23. Sartori P. Angew. Chem. 76 (1964) 376
24. Iranpoor N., and Zeynizadeh B. Synth. Commun. 28 (1998) 3913
25. Bandgar B.P., Joshi N.S., and Kamble V.T. Tetrahedron Lett. 47 (2006) 4775
26. Bellomo A., and Gonzalez D. Tetrahedron: Asymmetry 17 (2006) 474
27. Bellomo, A.; Giacomini, C.; Brena, B.; Seoane.G.; Gonzalez, D. Synth. Commun. 2007, in press.
28. Hudlicky T., Price J.D., Rulin F., and Tsunoda T. J. Am. Chem. Soc. 112 (1990) 9439
29. Hudlicky T., Tian X., Königsberger, Maurya R., Rouden J., and Fan B. J. Am. Chem. Soc. 118 (1996) 10752
30. Hudlicky T., Gonzalez D., and Gibson D.T. Aldrichim. Acta 32 (1999) 35
31. Ramesh K., Wolfe M.S., Lee Y., Vander Velde D., and Borchardt R.T. J. Org. Chem. 57 (1992) 5861
32. Nugent T.C., and Hudlicky T. J. Org. Chem. 63 (1998) 510
33. Hudlicky T., Luna H., Olivo H.F., Andersen C., Nugent T.C., and Price J.D. J. Chem. Soc., Perkin Trans. 1 (1991) 2907
34. Van Tamelen E.E. J. Am. Chem. Soc. 73 (1951) 3444
35. Nicolaou K.C., Prasad C.V.C., Somers P.K., and Hwang C.K. J. Am. Chem. Soc. 111 (1989) 5330
36. Iranpoor N., and Kohmarch G.A. Phosphorous, Sulfur Silicon 152 (1999) 135
37. Price C.C., and Kirk P.F. J. Am. Chem. Soc. 78 (1953) 2396
38. Harvey R. Synthesis (1972) 627
39. Kloc K., Kubicz F., and Mlochowski J. Heterocycles 22 (1984) 2517
40. Shanghi H., Nasseri M.A., and Nejad A.H. J. Mol. Catal. A-Chem. 206 (2003) 53
41. Shanghi H., Nasseri M.A., and Niknam K. J. Org. Chem. 66 (2001) 7287
42. Gao Y., and Sharpless K.B. J. Am. Chem. Soc. 110 (1988) 7538
43. Olszewski-Ortar A., Gros P., and Fort Y. Tetrahedron Lett. 50 (1997) 8699
44. Yadav J.S., Reddy B.V.S., and Reddy Ch.S. Tetrahedron Lett. 45 (2004) 1291
45. Culvenor C.C.J., Davies W., and Heath N.S. J. Chem. Soc. (1949) 282
46. Culvenor C.C.J., Davies W., and Pausacker K.H. J. Chem. Soc. (1946) 1050
47. Pettit D.J., and Helmkamp G.K. J. Org. Chem. 29 (1964) 2702
48. Goodman L., and Baker B.R. J. Am. Chem. Soc. 81 (1959) 4924
49. Takeda K., and Komeno T. Chem. Ind. (1962) 1793
50. Takeda K., Komeno T., Kawanami J., Ishihara S., Kadokawa H., Tokura H., and Itani H. Tetrahedron 21 (1965) 329
51. Lighter D.A., and Djerassi C. Tetrahedron 21 (1965) 583
52. Tori K., and Komeno T. Tetrahedron Lett. 2 (1975) 135
53. 2S C, 41.08; H, 4.21.
54. Jankowski K., and Harvey R. Synthesis (1972) 627
55. Wright S.W., and Nelson M.J. Bioorg. Med. Chem. Lett. 2 (1992) 1385
56. Van Tamelen E.E. Org. Syn. 32 (1952) 39 Soc. 1951, 73, 3444.