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Volumn 56, Issue 23, 2015, Pages 3503-3506

Toward the ABCD core of the calyciphylline A-type daphniphyllum alkaloids: Solvent non-innocence in neutral aminyl radical cyclizations

Author keywords

Alkaloid; Daphniphyllum; Deuterium labeling; N centered radical; Radical cascade; Solvent effect

Indexed keywords

ALKALOID DERIVATIVE; ALKENE; CALYCIPHYLLINE A; DAPHNIPHYLLUM ALKALOID; DEUTERIUM; NATURAL PRODUCT; RADICAL; UNCLASSIFIED DRUG;

EID: 84929951223     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2015.01.121     Document Type: Article
Times cited : (26)

References (56)
  • 3
    • 0002333319 scopus 로고
    • R.H.F. Manske, Academic Press New York
    • S. Yamamura, and Y. Hirata R.H.F. Manske, The Alkaloids Vol. 60 1975 Academic Press New York 41 81
    • (1975) The Alkaloids , vol.60 , pp. 41-81
    • Yamamura, S.1    Hirata, Y.2
  • 5
    • 84896142701 scopus 로고    scopus 로고
    • For a review of recent efforts toward the calyciphylline A-type alkaloids, see:, and references therein
    • For a review of recent efforts toward the calyciphylline A-type alkaloids, see: B. Kang, P. Jakubes, and D.J. Dixon Nat. Prod. Rep. 31 2014 550 562 and references therein
    • (2014) Nat. Prod. Rep. , vol.31 , pp. 550-562
    • Kang, B.1    Jakubes, P.2    Dixon, D.J.3
  • 6
    • 84894571917 scopus 로고    scopus 로고
    • Efforts published since Ref. 5, or toward other Daphniphyllum alkaloids, include: (a)
    • Efforts published since Ref. 5, or toward other Daphniphyllum alkaloids, include: (a) L. Wang, C. Xu, L. Chen, H. Xiaojiang, and D.Z. Wang Org. Lett. 16 2014 1076 1079
    • (2014) Org. Lett. , vol.16 , pp. 1076-1079
    • Wang, L.1    Xu, C.2    Chen, L.3    Xiaojiang, H.4    Wang, D.Z.5
  • 15
    • 47749133097 scopus 로고    scopus 로고
    • For information on prior cyclizations of neutral aminyl radicals, see: (a)
    • For information on prior cyclizations of neutral aminyl radicals, see: (a) S.Z. Zard Chem. Soc. Rev. 37 2008 1603 1618
    • (2008) Chem. Soc. Rev. , vol.37 , pp. 1603-1618
    • Zard, S.Z.1
  • 30
    • 84929944260 scopus 로고    scopus 로고
    • All reactions in this text are performed in the enantiomeric series relative to the natural product.
    • All reactions in this text are performed in the enantiomeric series relative to the natural product.
  • 40
    • 84929943174 scopus 로고    scopus 로고
    • See the Supporting information for details.
    • See the Supporting information for details.
  • 41
    • 84929954547 scopus 로고    scopus 로고
    • The mass of the corresponding imine is observed by LCMS of the crude reaction mixture.
    • The mass of the corresponding imine is observed by LCMS of the crude reaction mixture.
  • 42
    • 84929963181 scopus 로고    scopus 로고
    • The quaternary benzyl ammonium salt is observed by LCMS of the crude reaction mixture, implying the existence of BnCl.
    • The quaternary benzyl ammonium salt is observed by LCMS of the crude reaction mixture, implying the existence of BnCl.
  • 43
    • 84929947077 scopus 로고    scopus 로고
    • Reduction products are observed as a mixture of uncyclized and cyclized forms.
    • Reduction products are observed as a mixture of uncyclized and cyclized forms.
  • 48
    • 84929958439 scopus 로고
    • J.K. Kochi, Wiley New York
    • K.U. Ingold J.K. Kochi, Free Radicals Vol. 1 1973 Wiley New York 77
    • (1973) Free Radicals , vol.1 , pp. 77
    • Ingold, K.U.1
  • 53
    • 84929952290 scopus 로고    scopus 로고
    • Scales and isolated yields: 38 mg lactol, 64% yield; 109 mg lactol, 81% yield; 200 mg lactol, 96% yield.
    • Scales and isolated yields: 38 mg lactol, 64% yield; 109 mg lactol, 81% yield; 200 mg lactol, 96% yield.
  • 54
    • 84929945547 scopus 로고    scopus 로고
    • Average of 2 runs.
    • Average of 2 runs.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.