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Volumn 62, Issue 40, 2006, Pages 9446-9455

A general approach to crinine-type Amaryllidaceae alkaloids: total syntheses of (±)-haemanthidine, (±)-pretazettine, (±)-tazettine, and (±)-crinamine

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CRINAMINE; HAEMANTHIDINE; PRETAZETTINE; TAZETTINE; UNCLASSIFIED DRUG;

EID: 33747780396     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/j.tet.2006.07.027     Document Type: Article
Times cited : (37)

References (50)
  • 1
    • 77957033352 scopus 로고
    • Brossi A. (Ed), Academic, New York, NY
    • Martin S.F. In: Brossi A. (Ed). The Alkaloids Vol. 30 (1987), Academic, New York, NY 251-376
    • (1987) The Alkaloids , vol.30 , pp. 251-376
    • Martin, S.F.1
  • 2
    • 77956708370 scopus 로고    scopus 로고
    • Cordell G.A. (Ed), Academic, New York, NY
    • Hoshino O. In: Cordell G.A. (Ed). The Alkaloids Vol. 51 (1998), Academic, New York, NY 323-424
    • (1998) The Alkaloids , vol.51 , pp. 323-424
    • Hoshino, O.1
  • 8
    • 33747759487 scopus 로고    scopus 로고
    • Total syntheses of (±)-haemanthidine and (±)-pretazettine:
  • 13
    • 0023267914 scopus 로고
    • Formal total syntheses of (±)-haemanthidine and (±)-pretazettine:
    • Martin S.F., Davidsen S.K., and Puckette T.A. J. Org. Chem. 52 (1987) 1962-1972 Formal total syntheses of (±)-haemanthidine and (±)-pretazettine:
    • (1987) J. Org. Chem. , vol.52 , pp. 1962-1972
    • Martin, S.F.1    Davidsen, S.K.2    Puckette, T.A.3
  • 19
    • 33747777219 scopus 로고    scopus 로고
    • Total synthesis of (±)-tazettine:
  • 23
    • 0032557235 scopus 로고    scopus 로고
    • Total synthesis of (+)-tazettine, see Ref. 3j.
    • Rigby J.H., Cavezza A., and Heeg M.J. J. Am. Chem. Soc. 120 (1998) 3664-3670 Total synthesis of (+)-tazettine, see Ref. 3j.
    • (1998) J. Am. Chem. Soc. , vol.120 , pp. 3664-3670
    • Rigby, J.H.1    Cavezza, A.2    Heeg, M.J.3
  • 24
    • 1642318908 scopus 로고
    • Total synthesis of (±)-crinamine: Total synthesis of (+)-crinamine, see Refs. 3h and 3i.
    • Total synthesis of (±)-crinamine:. Isobe K., Taga J., and Tsuda Y. Tetrahedron Lett. 17 (1976) 2331-2334 Total synthesis of (+)-crinamine, see Refs. 3h and 3i.
    • (1976) Tetrahedron Lett. , vol.17 , pp. 2331-2334
    • Isobe, K.1    Taga, J.2    Tsuda, Y.3
  • 42
    • 33747779129 scopus 로고    scopus 로고
    • note
    • 13C NMR spectra of all intermediate compounds between 13 and 22 were broadened and complicated by the presence of amide conformational isomers. These results were similar to that intermediate for synthesize 6-epipretazettine and tazettine (Ref. 4c).
  • 46


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