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Volumn 3, Issue 22, 2001, Pages 3507-3510

A new total synthesis of the marine tunicate alkaloid lepadiformine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CARDIOVASCULAR AGENT; DYES, REAGENTS, INDICATORS, MARKERS AND BUFFERS; LEPADIFORMINE;

EID: 0035513471     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol010179y     Document Type: Article
Times cited : (59)

References (36)
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    • Pearson, W.H.1    Ren, Y.2
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    • For synthetic work on the cylindricines, see: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630. Molander, G. A.; Ronn, M. J. Org. Chem. 1999, 64, 5183. Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263.
    • (1997) J. Org. Chem. , vol.62 , pp. 5630
    • Snider, B.B.1    Liu, T.2
  • 13
    • 0344436088 scopus 로고    scopus 로고
    • For synthetic work on the cylindricines, see: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630. Molander, G. A.; Ronn, M. J. Org. Chem. 1999, 64, 5183. Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263.
    • (1999) J. Org. Chem. , vol.64 , pp. 5183
    • Molander, G.A.1    Ronn, M.2
  • 14
    • 0033615710 scopus 로고    scopus 로고
    • For synthetic work on the cylindricines, see: Snider, B. B.; Liu, T. J. Org. Chem. 1997, 62, 5630. Molander, G. A.; Ronn, M. J. Org. Chem. 1999, 64, 5183. Liu, J. F.; Heathcock, C. H. J. Org. Chem. 1999, 64, 8263.
    • (1999) J. Org. Chem. , vol.64 , pp. 8263
    • Liu, J.F.1    Heathcock, C.H.2
  • 16
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    • Brossi, A., Ed.; Academic Press: San Diego
    • (b) Hiemstra, H.; Speckamp, W. N. In The Alkaloids; Brossi, A., Ed.; Academic Press: San Diego, 1988; Vol. 32, p 271.
    • (1988) The Alkaloids , vol.32 , pp. 271
    • Hiemstra, H.1    Speckamp, W.N.2
  • 17
  • 25
    • 0032474797 scopus 로고    scopus 로고
    • For some related spirocyclizations leading to histrionicotoxins see, inter alia: Tanner, D.; Haeberg, L. Tetrahedron 1998, 54, 7907. Evans, D. A.; Thomas, E. W.; Cherpeck, R. E. J. Am. Chem. Soc. 1982, 104, 3695. David, M.; Dhimane, H.; Vanucci-Bacque, C.; Lhommet, G. Heterocycles 2001, 55, 941.
    • (1998) Tetrahedron , vol.54 , pp. 7907
    • Tanner, D.1    Haeberg, L.2
  • 26
    • 0019921510 scopus 로고
    • For some related spirocyclizations leading to histrionicotoxins see, inter alia: Tanner, D.; Haeberg, L. Tetrahedron 1998, 54, 7907. Evans, D. A.; Thomas, E. W.; Cherpeck, R. E. J. Am. Chem. Soc. 1982, 104, 3695. David, M.; Dhimane, H.; Vanucci-Bacque, C.; Lhommet, G. Heterocycles 2001, 55, 941.
    • (1982) J. Am. Chem. Soc. , vol.104 , pp. 3695
    • Evans, D.A.1    Thomas, E.W.2    Cherpeck, R.E.3
  • 27
    • 0035338986 scopus 로고    scopus 로고
    • For some related spirocyclizations leading to histrionicotoxins see, inter alia: Tanner, D.; Haeberg, L. Tetrahedron 1998, 54, 7907. Evans, D. A.; Thomas, E. W.; Cherpeck, R. E. J. Am. Chem. Soc. 1982, 104, 3695. David, M.; Dhimane, H.; Vanucci-Bacque, C.; Lhommet, G. Heterocycles 2001, 55, 941.
    • (2001) Heterocycles , vol.55 , pp. 941
    • David, M.1    Dhimane, H.2    Vanucci-Bacque, C.3    Lhommet, G.4
  • 28
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    • note
    • We are grateful to Dr. Louis Todaro (Hunter College, CUNY) for the X-ray analyses of compounds 14 and 20.
  • 32
    • 0041728568 scopus 로고    scopus 로고
    • note
    • The unprotected hydroxymethyl analogue of amino nitrile 24 could be prepared, but this compound could not be alkylated successfully with hexyl Grignard reagents or cuprates.
  • 33
    • 0042228962 scopus 로고    scopus 로고
    • note
    • However, we cannot distinguish between the structure shown in 24 and the epimeric one in which the cyano group is equatorial in a chair conformation.
  • 36
    • 0035515394 scopus 로고    scopus 로고
    • We thank Professor J. F. Biard for copies of the proton and carbon NMR spectra, as well as a sample of natural lepadiformine. We are also grateful to Professor Ray Funk for NMR spectra of synthetic lepadiformine free base (9) and the corresponding hydrochloride; see: Funk, R. L.; Greshock, T. L. Org. Lett. 2001, 3, 3511.
    • (2001) Org. Lett. , vol.3 , pp. 3511
    • Funk, R.L.1    Greshock, T.L.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.