Two-directional total synthesis of efomycine M and formal total synthesis of elaiolide

Tetrahedron

Volumn 64, Issue 21, 2008, Pages 4718-4735

  Barth, Roland ^a   Mulzer, Johann ^a  

^a UNIVERSITY OF VIENNA   (Austria)

Author keywords

[No Author keywords available]

Indexed keywords

ACID; EFOMYCINE M; ELAIOLIDE; IODINE DERIVATIVE; KETONE; LACTONE DERIVATIVE; NATURAL PRODUCT; UNCLASSIFIED DRUG;

ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CHEMICAL REACTION; DIASTEREOISOMER; DIMERIZATION; DRUG STRUCTURE; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORNER REACTION; INFRARED SPECTROSCOPY; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; REDUCTION; STEREOCHEMISTRY; STRUCTURE ANALYSIS; YONEMITSU YAMAGUCHI MACROLACTONIZATION;

EID: 42249099980     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2008.01.114     Document Type: Article

References (52)

1. Schön M.P., Krahn T., Schön M., Rodriguez M.-L., Antonicek H., Schultz J.E., Ludwig R.J., Zollner T.M., Bischoff E., Bremm K.-D., Schramm M., Henninger K., Kaufmann R., Gollnick H.P.M., Parker C.M., and Boehncke W.-H. Nat. Med. 8 (2002) 366
2. Varki A. Proc. Natl. Acad. Sci. U.S.A. 91 (1994) 7390
3. Springer T. Cell 76 (1994) 301
4. Butcher E.C., and Picker L.J. Science 272 (1996) 60
5. Hammann P., and Kretzschmar G. Z. Naturforsch., B 45 (1990) 515
6. Arcamone F.M., Bertazzoli C., Ghione M., and Scotti T.G. Giorn. Microbiol. 7 (1959) 207
7. Arai M. J. Antibiot. Ser. A 13 (1960) 46
8. Takahashi S., Arai M., and Ohki E. Chem. Pharm. Bull. 15 (1967) 1651
9. Takahashi S., Kurabayashi M., and Ohki E. Chem. Pharm. Bull. 15 (1967) 1657
10. Takahashi S., and Ohki E. Chem. Pharm. Bull. 15 (1967) 1726
11. Kaiser H., and Keller-Schierlein W. Helv. Chim. Acta 64 (1981) 407
12. Neupert-Laves K., and Dobler M. Helv. Chim. Acta 65 (1982) 262
13. Ley S.V., Neuhaus D., and Williams D.K. Tetrahedron Lett. 23 (1982) 1207
14. Cui C., Wang H., Han B., Cai B., Luo A., Song Y., and Zhou P. Zhongguo Kangshengsu Zazhi 26 (2001) 165
15. Lee S.-Y., Kim H.-S., Kim Y.-H., Han S.-B., Kim H.-M., Hong S.-D., and Lee J.-J. J. Microbiol. Biotechnol. 7 (1997) 272
16. Igarashi Y., Yoshida R., and Furumai T. Shokubutsu no Seicho Chosetus 37 (2002) 63
17. Ziegler F.E., and Tung J.S. J. Org. Chem. 56 (1991) 6530
18. Morita A., and Kuwahara S. Tetrahedron Lett. 48 (2007) 3163
19. Toshima K., Tatsuta K., and Kinoshita M. Tetrahedron Lett. 27 (1986) 4741
20. Toshima K., Tatsuta K., and Kinoshita M. Bull. Chem. Soc. Jpn. 61 (1988) 2369
21. Seebach D., Chow H.-F., Jackson R.F.W., Lawson K., Sutter M.A., Thaisrivongs S., and Zimmermann J. J. Am. Chem. Soc. 107 (1985) 5292
22. Evans D.A., and Fitch D.M. J. Org. Chem. 62 (1997) 454
23. Paterson I., Lombart H.-G., and Allerton C. Org. Lett. 1 (1999) 19
24. Paterson I., and Man J. Tetrahedron Lett. 38 (1997) 695
25. von Bonin A., Buchmann B., Bader B., Rausch A., Venstrom K., Schäfer M., Gründemann S., Günther J., Zorn L., Nubbemeyer R., Asadullah K., and Zollner T.M. Nat. Med. 12 (2006) 873
26. Bader B., von Bonin A., Buchmann B., Gay J., Gruendemann S., Guenther J., Schaefer M., Spelling T., Zollner T.M., and Zorn L. Tetrahedron Lett. 48 (2007) 5984
27. Barth R., and Mulzer J. Angew. Chem. 119 (2007) 5893
28. Barth R., and Mulzer J. Angew. Chem., Int. Ed. 46 (2007) 5791
29. Evans D.A., Ng H.P., Clark J.S., and Rieger D.L. Tetrahedron 48 (1992) 2127
30. Evans D.A., Chapman K.T., and Carreira E.M. J. Am. Chem. Soc. 110 (1988) 3560
31. Roush W.R. J. Am. Chem. Soc. 102 (1980) 1390
32. Weinreb amide 30 was a generous gift form Dr. S. Mickel, Novartis AG Basel.
33. Smith III A.B., Beauchamp T.J., LaMarche M.J., Kaufman M.D., Qiu Y., Arimoto H., Jones D.R., and Kobayashi K. J. Am. Chem. Soc. 122 (2000) 8654
34. Mickel S.J., Daeffler R., and Prikoszovich W. Org. Process Res. Dev. 9 (2005) 113
35. Evans D.A., Bartroli J., and Shih T.L. J. Am. Chem. Soc. 103 (1981) 2127
36. Evans D.A., Nelson J.V., Vogel E., and Taber T.R. J. Am. Chem. Soc. 103 (1981) 3099
37. Gage J.R., and Evans D.A. Org. Synth. 68 (1990) 83
38. Yano T., Himeno Y., Nozaki H., and Otera J. Tetrahedron Lett. 27 (1986) 4501
39. Su Q., Beeler A.B., Lobkovsky E., Porco Jr. J.A., and Panek J.S. Org. Lett. 5 (2003) 2149
40. Inagana J., Hirata K., Saeki H., Katsuki T., and Yamaguchi M. Bull. Chem. Soc. Jpn. 52 (1979) 1989
41. Tone H., Nishi T., Oikawa Y., Hikota M., and Yonemitsu O. Tetrahedron Lett. 28 (1987) 4569
42. Chow H.-F., Jackson R.F.W., Sutter M.A., and Seebach D. Liebigs Ann. Chem. 108 (1986) 7408
43. Miwa K., Aoyama T., and Shioiri T. Synlett (1994) 107
44. Hydrozirconation was performed according to the following procedure:. Huang Z., and Negishi E.-I. Org. Lett. 8 (2006) 3675
45. Nitta K., Utimoto K., and Takai K. J. Am. Chem. Soc. 108 (1986) 7408
46. For an excellent review see:. Fürstner A. Chem. Rev. 99 (1999) 991
47. Xu W., and Wipf P. Tetrahedron Lett. 35 (1994) 5197
48. Review:. Jahn H., and Wipf. Tetrahedron 52 (1996) 12853
49. Hanessian S., Delorme D., and Dufresne Y. Tetrahedron Lett. 25 (1984) 2515
50. An authentic sample of efomycine M (1) was obtained from Dr. B. Buchmann, Schering AG.
51. Tsuji J., Nagashima H., and Nemoto H. Org. Synth. 62 (1984) 9
52. Tsuji J. In: Trost B.M. (Ed). Comprehensive Organic Synthesis Vol. 7 (1991), Pergamon, Oxford 449