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Volumn 9, Issue 7, 2007, Pages 1367-1369

Highly convergent route to cyclopeptide alkaloids. Total synthesis of ziziphine N

Author keywords

[No Author keywords available]

Indexed keywords

ALKALOID; CYCLOPEPTIDE; UNCLASSIFIED DRUG; ZIZIPHINE N;

EID: 34147136056     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol070271f     Document Type: Article
Times cited : (59)

References (38)
  • 1
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    • For a recent review, see: a, For recent reports on isolation, see
    • For a recent review, see: (a) Gournelis, D. C.; Laskaris, O. G.; Verpoorte, R. Nat. Prod. Rep. 1997, 75-82. For recent reports on isolation, see:
    • (1997) Nat. Prod. Rep , pp. 75-82
    • Gournelis, D.C.1    Laskaris, O.G.2    Verpoorte, R.3
  • 7
    • 6344258480 scopus 로고    scopus 로고
    • For a comprehensive review, see
    • For a comprehensive review, see: Joullié, M. M.; Richard, D. J. Chem. Commun. 2004, 2011-2015.
    • (2004) Chem. Commun , pp. 2011-2015
    • Joullié, M.M.1    Richard, D.J.2
  • 8
    • 0018239479 scopus 로고
    • For macrocyclization studies, see: a, and references cited therein
    • For macrocyclization studies, see: (a) Lagarias, J. C.; Houghten, R. A.; Rapoport, H. J. Am. Chem. Soc. 1978, 100, 8202-8212 and references cited therein.
    • (1978) J. Am. Chem. Soc , vol.100 , pp. 8202-8212
    • Lagarias, J.C.1    Houghten, R.A.2    Rapoport, H.3
  • 24
    • 2942594724 scopus 로고    scopus 로고
    • For related studies, see
    • (a) Pan, X.; Cai, Q.; Ma, D. Org. Lett. 2004, 6, 1809-1812. For related studies, see:
    • (2004) Org. Lett , vol.6 , pp. 1809-1812
    • Pan, X.1    Cai, Q.2    Ma, D.3
  • 29
    • 19544380068 scopus 로고    scopus 로고
    • (f) Hu, T.; Li, C. Org. Lett. 2005, 7, 2035-2038.
    • (2005) Org. Lett , vol.7 , pp. 2035-2038
    • Hu, T.1    Li, C.2
  • 37
    • 34147165009 scopus 로고    scopus 로고
    • Selected data for 1: 1H NMR (500 MHz, CDCl3) δ 0.86 (d, J, 6.7 Hz, 3H, 0.94 (d, J, 6.9 Hz, 6H, 0.95 (t, J, 6.8 Hz, 3H, 1.14 (m, 1H, 1.48 (m, 2H, 1.56 (m, 1H, 1.64 (m, 1H, 1.75 (m, 2H, 1.94 (m, 2H, 2.24 (s, 6H, 2.36 (m, 1H, 2.46 (m, 1H, 2.55 (d, J, 5.6 Hz, 1H, 3.26 (m, 1H, 3.57 (m, 1H, 3.80 (s, 3H, 4.21 (m, 2H, 4.38 (d, J, 5.8 Hz, 1H, 4.52 (dd, J, 9.0, 4.2 Hz, 1H, 4.75 (dd, J, 7.9, 7.6 Hz, 1H, 5.94 (d, J, 8.8 Hz, 1H, 6.80 (br s, 1H, 6.82 (d, J, 7.3 Hz, 1H, 6.86 (d, J, 11.6 Hz, 1H, 6.92(dd, J, 11.5, 8.8 Hz, 1H, 6.94 (d, 7, 8.8 Hz, 1H, 8.34 (d, J, 11.5 Hz, 1H, 13CNMR (125 MHz, CDCl3) δ 11.7, 14.3, 21.4, 22.9, 24.4, 24.6, 26.7, 28.8, 32.4, 34.0, 40.6, 42.8, 45.1, 47.6 2C, 55.7, 61.8, 62.5, 74.1, 78.4, 106.4, 110.5, 113.6, 116.7, 121.4, 123.9, 150.7, 151.0, 167.5, 171.0, 171.3, 171.6; MS m/z 634.2 [M, Na
    • + 634.3575, found 634.3578.
  • 38
    • 33846522460 scopus 로고    scopus 로고
    • During the preparation of this manuscript, Evano and co-workers reported the synthesis of paliurine F, a structurally related alkaloid of ziziphine N, by using two Cu-catalyzed couplings. See
    • During the preparation of this manuscript, Evano and co-workers reported the synthesis of paliurine F, a structurally related alkaloid of ziziphine N, by using two Cu-catalyzed couplings. See: Toumi, M.; Couty, F.; Evano, G. Angew. Chem., Int. Ed. 2007, 46, 572-575.
    • (2007) Angew. Chem., Int. Ed , vol.46 , pp. 572-575
    • Toumi, M.1    Couty, F.2    Evano, G.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.