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Volumn 119, Issue 10, 1997, Pages 2446-2452

Total synthesis of (+)-isolaurepinnacin. Use of acetal-alkene cyclizations to prepare highly functionalized seven-membered cyclic ethers

Author keywords

[No Author keywords available]

Indexed keywords

ISOLAUREPINNACIN; OXEPANE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0030899135     PISSN: 00027863     EISSN: None     Source Type: Journal    
DOI: 10.1021/ja964080b     Document Type: Article
Times cited : (65)

References (55)
  • 1
    • 0002144535 scopus 로고
    • Scheuer, P. J., Ed.; Academic: New York
    • (a) Moore, R. E. In Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1978; Vol. 1, pp 43-121.
    • (1978) Marine Natural Products , vol.1 , pp. 43-121
    • Moore, R.E.1
  • 2
    • 0000359232 scopus 로고
    • Scheuer, P. J., Ed.; Academic: New York
    • (b) Erickson, K. L. In Marine Natural Products; Scheuer, P. J., Ed.; Academic: New York, 1983; Vol. 5, pp 131-257.
    • (1983) Marine Natural Products , vol.5 , pp. 131-257
    • Erickson, K.L.1
  • 3
    • 0030131103 scopus 로고    scopus 로고
    • and earlier reviews in this series
    • (c) Faulkner, D. J. Nat. Prod. Rep. 1996, 13, 75, and earlier reviews in this series.
    • (1996) Nat. Prod. Rep. , vol.13 , pp. 75
    • Faulkner, D.J.1
  • 17
    • 0002324898 scopus 로고
    • For reviews of vinylsilane-terminated cyclization reactions, see: (a) Fleming, I.; Dunogues, I.; Smithers, R. Org. React. 1989, 37, 57. (b) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986,86, 857. (c) Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
    • (1989) Org. React. , vol.37 , pp. 57
    • Fleming, I.1    Dunogues, I.2    Smithers, R.3
  • 18
    • 33845373996 scopus 로고
    • For reviews of vinylsilane-terminated cyclization reactions, see: (a) Fleming, I.; Dunogues, I.; Smithers, R. Org. React. 1989, 37, 57. (b) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986,86, 857. (c) Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
    • (1986) Chem. Rev. , vol.86 , pp. 857
    • Blumenkopf, T.A.1    Overman, L.E.2
  • 19
    • 0001816392 scopus 로고
    • For reviews of vinylsilane-terminated cyclization reactions, see: (a) Fleming, I.; Dunogues, I.; Smithers, R. Org. React. 1989, 37, 57. (b) Blumenkopf, T. A.; Overman, L. E. Chem. Rev. 1986,86, 857. (c) Overman, L. E. Lect. Heterocycl. Chem. 1985, 8, 59.
    • (1985) Lect. Heterocycl. Chem. , vol.8 , pp. 59
    • Overman, L.E.1
  • 20
    • 0000527199 scopus 로고
    • Inversion and rotation barriers of oxocarbenium ions are sufficiently low that reaction via only the more stable E stereoisomer is expected: Cremer, D.; Gauss, J.; Childs, R. F.; Blackburn, C. J. Am. Chem. Soc. 1985, 107, 2435.
    • (1985) J. Am. Chem. Soc. , vol.107 , pp. 2435
    • Cremer, D.1    Gauss, J.2    Childs, R.F.3    Blackburn, C.4
  • 51
    • 0022397622 scopus 로고    scopus 로고
    • (b) See also: Saksena, A. K.; Green, M. J.; Mangiaracina, P.; Wong, J. K.; Kreutner, W.; Gulbenkian, A. R. Tetrahedron Lett. 1985, 26, 6423. Melikyan, G. C.; Mineif, A.; Vostrowsky, O.; Bestmann, H. J. Synthesis 1991, 633.
    • Synthesis , vol.1991 , pp. 633
    • Melikyan, G.C.1    Mineif, A.2    Vostrowsky, O.3    Bestmann, H.J.4
  • 52
    • 1842289658 scopus 로고    scopus 로고
    • personal communication to L.E.O. on June 10, 1993. equation presented
    • Fukuzawa, A., personal communication to L.E.O. on June 10, 1993. equation presented.
    • Fukuzawa, A.1
  • 53
    • 1842293817 scopus 로고    scopus 로고
    • DowElanco Insect Management Research Group, personal communication to L.E.O., January 25, 1994
    • Gipson, R. W.; Pechacek, J. T. DowElanco Insect Management Research Group, personal communication to L.E.O., January 25, 1994.
    • Gipson, R.W.1    Pechacek, J.T.2
  • 54
    • 0028556311 scopus 로고
    • Unless noted otherwise, new compounds were nearly colorless oils. Temperatures refer to external bath temperatures unless noted otherwise. General experimental details have been described: Deng. W.; Overman, L. E. J. Am. Chem. Soc. 1994, 116, 11241.
    • (1994) J. Am. Chem. Soc. , vol.116 , pp. 11241
    • Deng, W.1    Overman, L.E.2
  • 55
    • 1842364774 scopus 로고    scopus 로고
    • note
    • 13C NMR spectrum: δ 63.3 (natural), 63.1 (epi), 61.7 (epi), 61.4 (natural).


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