A convergent total synthesis of epolactaene: An application of the bridgehead oxiranyl anion strategy

Tetrahedron

Volumn 59, Issue 49, 2003, Pages 9743-9758

  Kuramochi, Kouji ^a   Nagata, Seigo ^a   Itaya, Hideyoshi ^a   Matsubara, Yasuaki ^a   Sunoki, Takashi ^a   Uchiro, Hiromi ^a   Takao, Ken Ichi ^a,b   Kobayashi, Susumu ^a  

^a TOKYO UNIVERSITY OF SCIENCE   (Japan)

^b KEIO UNIVERSITY   (Japan)

Author keywords

Aldol reaction; Epolactaene; Epoxylactone; TBAF

Indexed keywords

ALDEHYDE; ANION; EPOLACTAENE; ETHYLENE OXIDE DERIVATIVE; LACTAM DERIVATIVE; LACTONE DERIVATIVE; TRIMETHYLSILYL EPOXYLACTONE; UNCLASSIFIED DRUG;

ALDOL REACTION; ARTICLE; CARBON NUCLEAR MAGNETIC RESONANCE; CATALYSIS; CHEMICAL REACTION; DRUG SYNTHESIS; HIGH PERFORMANCE LIQUID CHROMATOGRAPHY; HORNER WADSWORTH EMMONS REACTION; INFRARED SPECTROSCOPY; OXIDATION; PRIORITY JOURNAL; PROTON NUCLEAR MAGNETIC RESONANCE; SYNTHESIS; TANDEM MASS SPECTROMETRY; THIN LAYER CHROMATOGRAPHY;

EID: 0242475007     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2003.09.021     Document Type: Article

References (54)

1. (a) Kakeya H., Takahashi I., Okada G., Isono K., Osada H. J. Antibiot. 48:1995;733
2. (b) Kakeya H., Onozawa C., Sato M., Arai K., Osada H. J. Med. Chem. 40:1997;391.
3. (a) Hayashi Y., Narasaka K. Chem. Lett. 1998;313
4. (b) Hayashi Y., Kanayama J., Yamaguchi J., Shoji M. J. Org. Chem. 67:2002;9443
5. (c) Marumoto S., Kogen H., Naruto S. J. Org. Chem. 63:1998;2068
6. (d) Marumoto S., Kogen H., Naruto S. Tetrahedron. 55:1999;7129
7. (e) Marumoto S., Kogen H., Naruto S. Tetrahedron. 55:1999;7145.
8. (a) Kuramochi K., Itaya H., Nagata S., Takao K., Kobayashi S. Tetrahedron Lett. 40:1999;7367
9. (b) Kuramochi K., Nagata S., Itaya H., Takao K., Kobayashi S. Tetrahedron Lett. 40:1999;7371.
10. (a) Eisch J.J., Galle J.E. J. Org. Chem. 55:1990;4835
11. (b) Eisch J.J., Galle J.E. J. Organomet. Chem. 341:1988;293
12. (c) Eisch J.J., Galle J.E. J. Organomet. Chem. 121:1976;C10.
13. Fawcett F.S. Chem. Rev. 47:1950;219.
14. (a) Satoh T. Chem. Rev. 96:1996;3303
15. (b) Mori Y., Yaegashi K., Furukawa H. J. Am. Chem. Soc. 118:1996;8158
16. (c) Mani N.S., Townsend C.A. J. Org. Chem. 62:1997;636
17. (d) Mori Y., Yaegashi K., Furukawa H. J. Org. Chem. 63:1998;6200
18. (e) Lertvorachon J., Thebtaranonth Y., Thongpanchang T., Thongyoo P. J. Org. Chem. 66:2001;4692
19. (f) Capriati V., Degennaro L., Favia R., Florio S., Luisi R. Org. Lett. 4:2002;1551
20. (g) Satoh T., Shimura T., Sakai K. Heterocycles. 59:2003;137.
21. (a) Ortuno R.M., Cardellach J., Font J. J. Heterocycl. Chem. 24:1987;79
22. (b) Hildebrandt B., Nakamura Y., Ogawa S. Carbohydr. Res. 214:1991;87.
23. Kobrich G., Trapp H. Chem. Ber. 99:1966;680-688.
24. Dubuffet T., Sauvetre R., Normant J.F. Tetrahedron Lett. 29:1988;5923-5924.
25. 2O present in commercial THF solution of TBAF. We found that the addition of molecular sieves 3 Å instead of 4 Å was not effective affording the desilylated epoxylactone 2.
26. Without purification and separation, the crude mixture (5, aldehyde, and 10) was retreated with TBAF and MS4 Å, and this operation was repeated.
27. Noyori R., Nishida I., Sakata J. J. Am. Chem. Soc. 103:1981;2106.
28. (a) Beckmann M., Hildebrandt H., Winterfeldt E. Tetrahedron: Asymmetry. 1:1990;335
29. (b) Ito Y., Kobayashi Y., Kawabata T., Takase M., Terashima S. Tetrahedron. 45:1989;5767
30. (c) Takadoi M., Katoh T., Ishiwata A., Terashima S. Tetrahedron Lett. 40:1999;3399
31. (d) Takadoi M., Katoh T., Ishiwata A., Terashima S. Tetrahedron. 58:2002;9903.
32. (a) Ando K. Tetrahedron Lett. 36:1995;4105
33. (b) Ando K. J. Org. Chem. 62:1997;1934 Ando K. J. Org. Chem. 64:1999;8406.
34. (b) Ando K. J. Org. Chem. 62:1997;1934 Ando K. J. Org. Chem. 64:1999;8406.
35. (a) Kozikowski A.P., Jung S.H., Springer J.P. J. Chem. Soc., Chem. Commun. 1988;167
36. (b) Onoda T., Shirai R., Koiso Y., Iwasaki S. Tetrahedron. 52:1996;14543.
37. (a) Ahmed M., Barley G.C., Hern M.T.W., Jones E.R.H., Thaller V., Yates J.A. J. Chem. Soc. Perkin Trans. 1. 1981;1974
38. (b) Corey E.J., Ruden R.A. Tetrahedron Lett. 1973;1495.
39. Taylar E.C., Ray P.S. J. Org. Chem. 53:1988;35.
40. (a) van Horn D.E., Negishi E. J. Am. Chem. Soc. 100:1978;2252
41. (b) van Horn D.E., Valente L.F., Idacavage M.J., Negishi E. J. Organomet. Chem. Soc. 156:1978;C20
42. (c) Ndibwami A., Lamothe S., Guay D., Plante R., Sousy P., Goldsrein S., Delongchamps P. Can. J. Chem. 71:1993;695.
43. Ensley H.E., Buescher R.R., Lee K. J. Org. Chem. 47:1982;404.
44. Dalcanale E., Montanari F. J. Org. Chem. 51:1986;567.
45. (a) Stille J.K. Angew. Chem., Int. Ed. Engl. 25:1986;508.
46. (b) Farina V., Kapadia S., Krishnan B., Wang C., Liebeskind L.S. J. Org. Chem. 59:1994;5905.
47. Greene T.W., Wuts P.G.M. Protective Groups in Organic Synthesis. 2nd ed. 1991;Wiley, New York. p 53.
48. Mancuso A.J., Swern D. Synthesis. 1981;165.
49. Schlessinger R.H., Poss M.A., Richardson S., Lin P. Tetrahedron Lett. 26:1985;2391.
50. (a) Zdrojewski T., Jonczyk A. J. Org. Chem. 63:1998;452
51. (b) Sharma R.K., Fry J.L. J. Org. Chem. 48:1983;2112.
52. Dess D.B., Martin J.C. J. Am. Chem. Soc. 113:1991;7277.
53. Mizushina Y., Kobayashi S., Kuramohi K., Nagata S., Sugawara F., Sakaguchi K. Biochem. Biophys. Res. Commun. 273:2000;784.
54. Nakai J., Kawada K., Nagata S., Kuramochi K., Uchiro H., Kobayashi S., Ikekita M. Biochim. Biophys. Acta. 1581:2002;1.