Examination of the olefin-olefin ring closing metathesis to prepare Latrunculin B

Tetrahedron Letters

Volumn 50, Issue 3, 2009, Pages 298-301

  She, Jin ^a   Lampe, John W ^a   Polianski, Alexandra B ^a   Watson, Paul S ^a  

^a MERCK RESEARCH LABORATORIES   (United States)

Author keywords

[No Author keywords available]

Indexed keywords

ALKENE; LACTONE DERIVATIVE; LATRUNCULIN B; MACROCYCLIC COMPOUND;

ARTICLE; CATALYST; CHEMICAL REACTION; CHEMICAL STRUCTURE; CYCLIZATION; POLYMERIZATION; REACTION ANALYSIS; RING CLOSING METATHESIS; STEREOCHEMISTRY; SYNTHESIS;

EID: 57149136022     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2008.10.144     Document Type: Article

References (38)

1. Oliveira C.A., Kashman Y., and Mantovani B. Chem.-Biol. Interact. 100 (1996) 141-153
2. Blasberger D., Carmely S., Cojocaru M., Spector I., Shochet N.R., and Kashman Y. Liebigs Ann. Chem. 12 (1989) 1171-1188
3. Kashman, Y.; Spector, I.; Carmely, S.; Blasberger, D. U.S. 4857538 A, 1989, 6 p.
4. Spector I., Shochet N.R., Blasberger D., and Kashman Y. Cytoskeleton 13 (1989) 127-144
5. Blasberger D., Green D., Carmely S., Spector I., and Kashman Y. Tetrahedron Lett. 28 (1987) 459-462
6. Kashman Y., Lidor R., Blasberger D., and Carmely S. Tetrahedron Lett. 27 (1986) 1367-1370
7. Kashman Y., Groweiss A., Lidor R., Blasberger D., and Carmely S. Tetrahedron 41 (1985) 1905-1914
8. Groweiss A., Shmueli U., and Kashman Y. J. Org. Chem. 48 (1983) 3512-3516
9. Spector I., Shochet N.R., Kashman Y., and Groweiss A. Science 219 (1983) 493-495
10. Kashman Y., Groweiss A., and Shmueli U. Tetrahedron Lett. 21 (1980) 3629-3632
11. Nèeman I., Fishelson L., and Kashman Y. Mar. Biol. 30 (1975) 293-296
12. Smith III A.B., Leahy J.W., Noda I., Remiszewski S.W., Liverton N.J., and Zibuck R. J. Am. Chem. Soc. 114 (1992) 2995-3007
13. Smith III A.B., Noda I., Remiszewski S.W., Liverton N.J., and Zibuck R. J. Org. Chem. 55 (1990) 3977-3979
14. Smith, A. B. III; Zibuck, R.; Liverton, N. J. Studies in Organic Chemistry (Amsterdam, 1986), 25 (New Synth. Methodol. Funct. Interesting Compd.), 183-202.
15. Zibuck R., Liverton N.J., and Smith III A.B. J. Am. Chem. Soc. 108 (1986) 2451-2453
16. White J.D., and Kawasaki M. J. Org. Chem. 57 (1992) 5292-5300
17. White J.D., and Kawasaki M. J. Am. Chem. Soc. 112 (1990) 4991-4993
18. For selected reviews see:. Gradillas A., and Périz-Castells J. Angew. Chem., Int. Ed. Engl. 45 (2006) 6086-6101
19. Grubbs R.H., and Chang S. Tetrahedron 54 (1998) 4413-4450
20. Armstrong S.K. J. Chem. Soc., Perkin Trans. 1 (1998) 371-388
21. Fürstner A., Nagano T., Mueller C., Seidel G., and Mueller O. Chem.-A Eur. J. 13 (2007) 1452-1462
22. Fürstner A., Kirk D., Fenster M.D.B., Aiessa C., De Souza D., Nevado C., Tuttle T., Thiel W., and Mueller O. Chem.-A Eur. J. 13 (2006) 135-149
23. Fürstner A., De Souza D., Turet L., Fenster M.D.B., Parra-Rapado L., Wirtz C., Myott R., and Lehmann C.W. Chem.-A Eur. J. 13 (2006) 115-134
24. Fürstner A., Kirk D., Fenster M.D.B., Aissa C., De Souza D., and Mueller O. PNAS 102 (2005) 8103-8108
25. Fürstner A., and Turet L. Angew. Chem., Int. Ed. Engl. 44 (2005) 3462-3466
26. Fürstner A., De Souza D., Parra-Rapado L., and Jensen J.T. Angew. Chem., Int. Ed. Engl. 42 (2003) 5358-5360
27. Kaufman, P. L.; Geiger, B. PCT Int. Appl. WO 9730701, 1997, 65 p.
28. Peterson J.A., Tian B., Geiger B., and Kaufman P.L. Exp. Eye Res. 70 (2000) 307-313
29. Priebe H., and Hopf H. Angew. Chem., Int. Ed. Engl. 21 (1982) 286
30. Crimmins M.T., and Shamszad M. Org. Lett. 9 (2007) 149-152
31. Zhang Y., Phillips A.J., and Sammakia T. Org. Lett. 6 (2004) 23-25
32. Romero-Ortega M., Colby D.A., and Olivo H.F. Tetrahedron Lett. 43 (2002) 6439-6441
33. Nagao Y., and Hagiwara Y. J. Org. Chem. 51 (1986) 2391-2393
34. Paquette L.A., and Maynard G.D. J. Am. Chem. Soc. 114 (1992) 5018-5027
35. Thiazolidinethione acetate 12 can be produced by following the procedure to make thiazolidinethione propionate:. Crimmins M.T., and Chaudhary K. Org. Lett. 2 (2000) 775
36. Furstner A., and Langemann K. Synthesis (1997) 792-803
37. Lee C.W., and Grubbs R.H. Org. Lett. 2 (2000) 2145-2147
38. Meng D., Su D.-S., Balog A., Bertinato P., Sorenson E.J., Danishefsky S.J., Zheng Y.-H., Chou T.-C., He L., and Horwitz S.B. J. Am. Chem. Soc. 119 (1997) 2733-2734