Synthesis of the C21-C28 segment of pectenotoxin-4

Tetrahedron Letters

Volumn 48, Issue 27, 2007, Pages 4761-4764

  Kolakowski, Robert V ^a   Williams, Lawrence J ^a  

^a RUTGERS UNIVERSITY   (United States)

Author keywords

Marshall cyclization; Pectenotoxin; Tetrahydrofuran synthesis; Weinreb amide

Indexed keywords

ALKYNE; AMIDE; MACROLIDE; PECTENOTOXIN 4; UNCLASSIFIED DRUG;

ALKYNYLATION; ARTICLE; BIOLOGICAL ACTIVITY; DRUG STRUCTURE; DRUG SYNTHESIS; ROOM TEMPERATURE;

EID: 34249911751     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.148     Document Type: Article

References (50)

1. Yasumoto T., Murata M., Oshima Y., Sano M., Matsumoto K.G., and Clardy J. Tetrahedron 41 (1985) 1019
2. Zhou Z.-H., Komiyama M., Terao K., and Shimada Y. Nat. Toxins 2 (1994) 132
3. Leira F., Cabado A.G., Vieytes M.R., Roman Y., Alfonso A., Botana L.M., Yasumoto T., Malaguti C., and Rossini G.P. Biochem. Pharmacol. 63 (2002) 1979
4. Review:. Allingham J.S., Klenchin V.A., and Rayment I. Cell Mol. Life Sci. 63 (2006) 2119
5. Hung J.H., and Sim C.J. J. Nat. Prod. 58 (1995) 1722
6. Chae H.-D., Choi T.-S., Kim B.-M., Jung J.H., Bang Y.-J., and Shin D.Y. Oncogene 24 (2005) 4813
7. Synthetic approaches:. Halim R., Brimble M.A., and Merten J. Org. Lett. 7 (2005) 2659
8. Bondar D., Liu J., Muller T., and Paquette L.A. Org. Lett. 7 (2005) 1813
9. Peng X., Bondar D., and Paquette L.A. Tetrahedron 60 (2004) 9589
10. Paquette L.A., Peng X., and Bondar D. Org. Lett. 4 (2002) 937
11. Micalizio G.C., and Roush W.R. Org. Lett. 3 (2001) 1949
12. Amano S., Fujiwara K., and Murai A. Synlett (1997) 1300
13. Fujiwara K., Kobayashi M., Yamamoto F., Aki Y., Kawamura M., Awakura D., Amano S., Okano A., Murai A., Kawai H., and Suzuki T. Tetrahedron Lett. 46 (2005) 5067
14. O'Connor P.D., Knight C.K., Friedrich D., Peng X., and Paquette L.A. J. Org. Chem. 72 (2007) 1747
15. Lotesta S.D., Hou Y., and Williams L.J. Org. Lett. 9 (2007) 869
16. Pihko P.M., and Aho J.E. Org. Lett. 6 (2004) 3849
17. Vellucci D., and Rychnovsky S.D. Org. Lett. 9 (2007) 711
18. Total synthesis:. Evans D.A., Rajapakse H.A., and Stenkamp D. Angew. Chem., Int. Ed. 41 (2002) 4569
19. Evans D.A., Rajapakse H.A., Chiu A., and Stenkamp D. Angew. Chem., Int. Ed. 41 (2002) 4573
20. Tokunga M., Larrow J.F., Kakiuchi F., and Jacobsen E.N. Science 936 (1997) 277
21. Furrow M.E., Schaus S.E., and Jacobsen E.N. J. Org. Chem. 63 (1998) 6776
22. Dale J.A., Dull D.L., and Mosher H.S. J. Org. Chem. 34 (1969) 2543
23. Preparation of trichloroacetimidates:. Wessel H.-P., Iverson T., and Bundle D.R. J. Chem. Soc., Perkin Trans. 1 (1985) 2247
24. Hydroxyl protection:. Nakajima N., Horita K., Abe R., and Yonemitsu O. Tetrahedron Lett. (1988) 4139
25. Mancuso A.J., Huang S.-L., and Swern D. J. Org. Chem. 43 (1978) 2481
26. General procedure:. Fernández M., and Tojo G. Oxidation of Alcohol to Aldehydes and Ketones (2006), Springer, New York p 141
27. Selective reduction of A proved to be an inferior alternative; treatment of A with DiBAl-H in toluene or sodium cyanoborohydride and TMSCl in acetonitrile gave a 1:1 mixture of regioisomers:. Takano S., Akiyama M., Sato S., and Ogasawara K. Chem. Lett. (1983) 1593
28. Johansson R., and Samuelsson B. J. Chem. Soc., Perkin Trans. 1 (1984) 2371 {A figure is presented}
29. Stereochemical assignment of the alkylation product is based on analogy to:. Evans D.A., Ennis M.D., and Mathre D.J. J. Am. Chem. Soc. 104 (1982) 1737
30. Lerm M., Gais H.-J., Cheng K., and Vermeeren C. J. Am. Chem. Soc. 125 (2003) 9653
31. Cherest M., Felkin H., and Prudent N. Tetrahedron Lett. 18 (1968) 2199
32. Cherest M., and Felkin H. Tetrahedron Lett. 18 (1968) 2205
33. Anh N.T., and Eisenstein O. Nouv. J. Chim. 1 (1977) 61
34. Shimizu M., Kawamoto M., and Niwa Y. Chem. Commun. (1999) 1151
35. For a review of alkynylation of chiral aldehydes see:. Guillarme S., Plé K., Banchet A., Liard A., and Haudrechey A. Chem. Rev. 106 (2006) 2355
36. Bhupathy M., and Cohen T. Tetrahedron Lett. 26 (1985) 2619
37. Frantz D.E., Fassler R., and Carreira E.M. J. Am. Chem. Soc. 122 (2000) 1806
38. El-Sayed E., Anand N.K., and Carreira E.M. Org. Lett. 3 (2001) 3017
39. Marshall J.A., and Pinney K.G. J. Org. Chem. 58 (1993) 7180
40. Nahm S., and Weinreb S.M. Tetrahedron Lett. 22 (1981) 3815
41. Marshall J.A., and Yanik M.M. J. Org. Chem. 66 (2001) 1373
42. Bourbeau M.P., and Marshall J.A. Org. Lett. 5 (2003) 3197
43. Shimizu T., Kusaka J., Ishiyama H., and Nakata T. Tetrahedron Lett. 44 (2003) 4695
44. Lerm M., Gais H.-J., Cheng K., and Vermeeren C. J. Am. Chem. Soc. 125 (2003) 9653
45. Klein M., Zabel M., Bernhardt G., and Burkhard K. J. Org. Chem. 68 (2003) 9379
46. Shin Y., Fournier J.-H., Fukui Y., Bruckner A.M., and Curran P.D. Angew. Chem., Int. Ed. 43 (2004) 4634
47. Rauhala V., Nattinen K., Rissanen K., and Koskinen A.M.P. Eur. J. Org. Chem. (2005) 4119
48. Shimizu T., Satoh T., Murakoshi K., and Sodeoka M. Org. Lett. 7 (2005) 5573
49. Pan Y., and De Brabander J.K. Synlett (2006) 0853
50. Acronyms and abbreviations: DDQ = dichloro dicyano quinone, DiBAl-H = diisobutylaluminum hydride, DMAP = 4-(N,N-Dimethylamino)pyridine, DMSO = dimethyl sulfoxide, EtOAc = ethyl acetate, LiHMDS = lithium hexamethyldisilazane, MeOH = methanol, MsCl = mesyl chloride, PivCl = pivaloyl chloride, TBDPSCl = tert-butyldiphenylsilyl chloride, TEA = triethylamine, TfOH = triflic acid, THF = tetrahydrofuran, TPAP = tetrapropylammonium perruthenate.