메뉴 건너뛰기




Volumn 26, Issue 5, 1996, Pages 935-944

A practical asymmetric synthesis of a pseudomonic acid precursor from D-arabinose or D-xylose

Author keywords

[No Author keywords available]

Indexed keywords

PSEUDOMONIC ACID; PYRAN DERIVATIVE;

EID: 0029941258     PISSN: 00397911     EISSN: None     Source Type: Journal    
DOI: 10.1080/00397919608003698     Document Type: Article
Times cited : (17)

References (30)
  • 2
    • 37049080594 scopus 로고
    • (a) Forrest, A. K.; O'Hanlon, P. J.; Walker, G. J. Chem. Soc. Perkin Trans. 1994, 21, 2657; Tetrahedron 1994, 36, 10739;
    • (1994) Tetrahedron , vol.36 , pp. 10739
  • 8
    • 9344219939 scopus 로고
    • in press
    • (f) For a recent review of pseudomonic acid syntheses see Class, Y. J.; DeShong, P. Chem. Rev. 1995 in press.
    • (1995) Chem. Rev.
    • Class, Y.J.1    DeShong, P.2
  • 11
    • 33847086734 scopus 로고
    • (b) Kozikowski, A. P.; Schmiesing, R. J.; Sorgi, K. L. J. Am. Chem. Soc. 1980, 102, 6577; Tetrahedron Lett. 1981, 2059;
    • (1981) Tetrahedron Lett. , pp. 2059
  • 12
    • 0000131109 scopus 로고
    • (c) Snider, B. B; Rodini, R. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927; Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555; Snider, B. B.; Phillips, G. B. J. Am. Chem. Soc. 1982, 104, 1113.; Snider, B. B.; Phillips, G. B.; Cordova, R. J. Org. Chem. 1983, 48, 3003;
    • (1981) Tetrahedron , vol.37 , pp. 3927
    • Snider, B.B.1    Rodini, R.J.2    Karras, M.3    Kirk, T.C.4    Deutsch, E.A.5    Cordova, R.6    Price, R.T.7
  • 13
    • 0019928219 scopus 로고
    • (c) Snider, B. B; Rodini, R. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927; Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555; Snider, B. B.; Phillips, G. B. J. Am. Chem. Soc. 1982, 104, 1113.; Snider, B. B.; Phillips, G. B.; Cordova, R. J. Org. Chem. 1983, 48, 3003;
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 555
    • Snider, B.B.1    Rodini, D.J.2    Kirk, T.C.3    Cordova, R.4
  • 14
    • 0020065021 scopus 로고
    • (c) Snider, B. B; Rodini, R. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927; Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555; Snider, B. B.; Phillips, G. B. J. Am. Chem. Soc. 1982, 104, 1113.; Snider, B. B.; Phillips, G. B.; Cordova, R. J. Org. Chem. 1983, 48, 3003;
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 1113
    • Snider, B.B.1    Phillips, G.B.2
  • 15
    • 0021063601 scopus 로고
    • (c) Snider, B. B; Rodini, R. J.; Karras, M.; Kirk, T. C.; Deutsch, E. A.; Cordova, R.; Price, R. T. Tetrahedron 1981, 37, 3927; Snider, B. B.; Rodini, D. J.; Kirk, T. C.; Cordova, R. J. Am. Chem. Soc. 1982, 104, 555; Snider, B. B.; Phillips, G. B. J. Am. Chem. Soc. 1982, 104, 1113.; Snider, B. B.; Phillips, G. B.; Cordova, R. J. Org. Chem. 1983, 48, 3003;
    • (1983) J. Org. Chem. , vol.48 , pp. 3003
    • Snider, B.B.1    Phillips, G.B.2    Cordova, R.3
  • 16
    • 0001207304 scopus 로고
    • (d) Fleet, G.W.J.; Spensley, C. R. C. Tetrahedron Lett. 1982, 109; Fleet G. W. J.; Gough, M. J. Tetrahedron Lett. 1982, 4509; Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1983, 3661.;
    • (1982) Tetrahedron Lett. , pp. 109
    • Fleet, G.W.J.1    Spensley, C.R.C.2
  • 17
    • 0000902201 scopus 로고
    • (d) Fleet, G.W.J.; Spensley, C. R. C. Tetrahedron Lett. 1982, 109; Fleet G. W. J.; Gough, M. J. Tetrahedron Lett. 1982, 4509; Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1983, 3661.;
    • (1982) Tetrahedron Lett. , pp. 4509
    • Fleet, G.W.J.1    Gough, M.J.2
  • 18
    • 0000056607 scopus 로고
    • (d) Fleet, G.W.J.; Spensley, C. R. C. Tetrahedron Lett. 1982, 109; Fleet G. W. J.; Gough, M. J. Tetrahedron Lett. 1982, 4509; Fleet, G. W. J.; Gough, M. J.; Shing, T. K. M. Tetrahedron Lett. 1983, 3661.;
    • (1983) Tetrahedron Lett. , pp. 3661
    • Fleet, G.W.J.1    Gough, M.J.2    Shing, T.K.M.3
  • 23
    • 85035163518 scopus 로고    scopus 로고
    • note
    • 2O to the allyl silane and arabinal at -78°C gave more reliable results.
  • 24
    • 85035164647 scopus 로고    scopus 로고
    • note
    • Xylal can be synthesized by the same route (Scheme 2) as arabinal with similar results.
  • 29
    • 85083243520 scopus 로고
    • Tsuji, J.; Shimaza, I.; Yamamoto, K. Tetrahedron Lett. 1976, 2975. Tsuji, J. Synthesis 1984, 369.
    • (1984) Synthesis , pp. 369
    • Tsuji, J.1
  • 30
    • 85035162254 scopus 로고    scopus 로고
    • note
    • Compounds 10 and 11 were further purified by HPLC but neither compound could be isolated in completely pure form.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.