Synthesis of the C8-C20 and C21-C30 segments of pectenotoxin 2

Tetrahedron Letters

Volumn 48, Issue 26, 2007, Pages 4523-4527

  Fujiwara, Kenshu ^a   Aki, Yu ichi ^a   Yamamoto, Fuyuki ^a   Kawamura, Mariko ^a   Kobayashi, Masanori ^a   Okano, Azusa ^a   Awakura, Daisuke ^a   Shiga, Shunsuke ^a   Murai, Akio ^a   Kawai, Hidetoshi ^a   Suzuki, Takanori ^a  

^a HOKKAIDO UNIVERSITY   (Japan)

Author keywords

Natural product synthesis; Pectenotoxin 2; Polyether macrolide

Indexed keywords

3 METHYL 3 BUTENOL; GLYCIDOL; MALIC ACID; PECTENOTOXIN 2; PHOSPHONIC ACID DERIVATIVE; TOXIN; UNCLASSIFIED DRUG;

ARTICLE; DIARRHEA; EPOXIDATION; FUNCTIONAL ANATOMY; HORNER WADSWORTH EMMONS REACTION; METHYLATION; REACTION ANALYSIS; REDUCTION KINETICS; SHELLFISH; STEREOCHEMISTRY; SYNTHESIS; TOXIN ANALYSIS;

EID: 34249288615     PISSN: 00404039     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tetlet.2007.04.136     Document Type: Article

References (57)

1. Yasumoto T., Murata M., Oshima Y., Sano M., Matsumoto G.K., and Clardy J. Tetrahedron 41 (1985) 1019
2. Sasaki K., Wright J.L.C., and Yasumoto T. J. Org. Chem. 63 (1998) 2475
3. Sasaki K., Satake M., and Yasumoto T. Biosci. Biotech. Biochem. 61 (1997) 1783
4. Ishige M., Sato N., and Yasumoto T. Rep. Hokkaido Inst. Public Health 38 (1988) 15
5. Terao K., Ito E., Yanagi T., and Yasumoto T. Toxicon 24 (1986) 1141
6. Jung J.H., Sim C.J., and Lee C.-O. J. Nat. Prod. 58 (1995) 1722
7. Zhou Z.-H., Komiyama M., Terao K., and Shimada Y. Nat. Toxins 2 (1994) 132
8. Hori M., Matsuura Y., Yoshimoto R., Ozaki H., Yasumoto T., and Karaki H. Folia Pharmacol. Jpn. 114 (1999) 225
9. Spector I., Braet F., Chochet N., and Bubb M.R. Microsc. Res. Technol. 47 (1999) 18
10. 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
11. The total synthesis of pectenotoxins-4 and -8, see:. Evans D.A., Rajapakse H.A., and Stenkamp D. Angew. Chem., Int. Ed. 41 (2002) 4569
12. Evans D.A., Rajapakse H.A., Chiu A., and Stenkamp D. Angew. Chem., Int. Ed. 41 (2002) 4573
13. Other synthetic studies, see:. Micalizino G.C., and Roush W.R. Org. Lett. 3 (2001) 1949
14. Paquette L.A., Peng X., and Bonder D. Org. Lett. 4 (2002) 937
15. Pihko P.M., and Aho J.E. Org. Lett. 6 (2004) 3849
16. Peng X., Bonder D., and Paquette L.A. Tetrahedron 60 (2004) 9589
17. Bonder D., Liu J., Muller T., and Paquette L.A. Org. Lett. 7 (2005) 1813
18. Halim R., Brimble M.A., and Merten J. Org. Lett. 7 (2005) 2659
19. Halim R., Brimble M.A., and Merten J. Org. Biomol. Chem. 4 (2006) 1387
20. Vellucci D., and Rychnovsky S.D. Org. Lett. 9 (2007) 711
21. Lotesta S.D., Hou Y., and Williams L.J. Org. Lett. 9 (2007) 369
22. O'Connor P.D., Knight C.K., Friedrich D., Peng X., and Paquette L.A. J. Org. Chem. 72 (2007) 1747
23. A review, see:. Halim R., and Brimble M.A. Org. Biomol. Chem. 4 (2006) 4048
24. Amano S., Fujiwara K., and Murai A. Synlett (1997) 1300
25. Awakura D., Fujiwara K., and Murai A. Synlett (2000) 1733
26. 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
27. Evans D.A., Ennis M.D., and Mathre D.J. J. Am. Chem. Soc. 104 (1982) 1737
28. Fukuyama T., Varanesic B., Negri D.P., and Kishi Y. Tetrahedron Lett. 19 (1978) 2741
29. Hayashi H., Nakanishi K., Brandon C., and Marmur J. J. Am. Chem. Soc. 95 (1973) 8749
30. Mori Y., Takeuchi A., Kageyama H., and Suzuki M. Tetrahedron Lett. 29 (1988) 5423
31. Clive D.L.J., Murthy K.S.K., Wee A.G.H., Prasad J.S., da Silva G.V.J., Majewski M., Anderson P.C., Evans C.F., Haugen R.D., Heerze L.D., and Barrie J.R. J. Am. Chem. Soc. 112 (1990) 3018
32. Mancuso A.J., Huang S.-L., and Swern D. J. Org. Chem. 43 (1978) 2048
33. Nakata T., and Oishi T. Tetrahedron Lett. 21 (1980) 1641
34. The absolute stereochemistry at C11 of 8 was determined by new Mosher's method:. Ohtani I., Kusumi T., Kashman Y., and Kakisawa H. J. Am. Chem. Soc. 113 (1991) 4092
35. Rossiter B.E., Verhoeven T.R., and Sharpless K.B. Tetrahedron Lett. 20 (1979) 4733
36. Tomioka H., Suzuki T., Nozaki H., and Oshima K. Tetrahedron Lett. 23 (1982) 3387
37. 3 of isopropyridene acetal 52 derived from 18 via 21 (Fig. 2).
38. Ide M., and Nakata M. Bull. Chem. Soc. Jpn. 72 (1999) 2491
39. Fujita E., Nagao Y., and Kaneko K. Chem. Pharm. Bull. 26 (1978) 3743
40. The use of 2,6-di-tert-butylpyridine was essential to obtain reproducible result.
41. Dess D.B., and Martin J.C. J. Org. Chem. 48 (1983) 4155
42. Dess D.B., and Martin J.C. J. Am. Chem. Soc. 113 (1991) 7277
43. Katsuki T., and Sharpless K.B. J. Am. Chem. Soc. 102 (1980) 5974
44. The optical yield of 11 was determined by HPLC using a chiral column [Daicel Chiralcel AD, eluent: hexane/2-propanol (9:1)].
45. 3, c 0.5): Krohn, K.; Meyer, A. Liebigs Ann. Chem. 1994, 167}.
46. Griffith W.P., and Ley S.V. Aldrichim. Acta 23 (1990) 13
47. Luche J.-L., and Gemal A.L. J. Am. Chem. Soc. 101 (1979) 5848
48. The absolute stereochemistry at C14 of 33 was determined by new Mosher's method. See Ref. 13.
49. The presence of the TMS group at C12-oxygen reduced stereoselectivity of the epoxidation step.
50. 3, and between H16 and H19 in 37 (Fig. 3).
51. We found that a primary alkyl DMB ether was readily removed on treatment with TMSOTf/2,6-lutidine. This phenomenon was helpful for selective detachment of the DMB group of 37 in the presence of the PMB ether at C11. On the other hand, detachment of a DMB group from 29 during TMS ether formation was avoided by lowering the reaction temperature (Scheme 3). cf. Oriyama T., Yatabe K., Kawada Y., and Koga G. Synlett (1995) 45
52. Walker K.A.M. Tetrahedron Lett. 18 (1977) 4475
53. +]: 1192.6196; found, 1192.6213.
54. 3.
55. Koch S.S.C., and Chamberlin A.R. J. Org. Chem. 58 (1993) 2725
56. 2, imidazole; (ii) Mg; (iii) DDQ, (iv) m-CPBA (yielding an almost single diastereomer); (v) CSA.] (Fig. 4).
57. +]: 348.2301; found, 348.2300.