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Volumn 53, Issue 7, 2012, Pages 876-878

Total synthesis of (-)-indolizidine 167B via an unusual Wolff rearrangement from an α,β-unsaturated diazoketone

Author keywords

Arndt Eistert homologation; Indolizidine alkaloids; Photochemical; Unsaturated diazoketones; Wolff rearrangement

Indexed keywords

CONICEINE; INDOLIZIDINE ALKALOID; KETONE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 84855851584     PISSN: 00404039     EISSN: 18733581     Source Type: Journal    
DOI: 10.1016/j.tetlet.2011.12.029     Document Type: Article
Times cited : (35)

References (26)
  • 8
    • 27844526992 scopus 로고    scopus 로고
    • Most publications describe indolizidines 167B and 209D as natural. However, according to Daly's recent reviews, the two isolated natural alkaloids (proposed tentatively to be indolizidines 167B and 209D) were found to be 3,5-disubstituted pyrrolizidines and were, therefore, tabulated as indolizidines 167F and 209K in the appendix. The code names 167B and 209D are maintained for the synthetic indolizidines, although they have not yet been detected in nature. Please see: J.W. Daly, T.F. Spande, and H.M. Garraffo J. Nat. Prod. 68 2005 1556
    • (2005) J. Nat. Prod. , vol.68 , pp. 1556
    • Daly, J.W.1    Spande, T.F.2    Garraffo, H.M.3
  • 13
    • 0025023824 scopus 로고
    • For the first asymmetric total synthesis of indolizidine 167B and 209D see: R.P. Polniaszek, and S.E. Belmont J. Org. Chem. 55 1990 4688
    • (1990) J. Org. Chem. , vol.55 , pp. 4688
    • Polniaszek, R.P.1    Belmont, S.E.2
  • 14
    • 80052810150 scopus 로고    scopus 로고
    • For recent examples of the asymmetric synthesis of indolizidine 167B and 209D see: R. Lazzaroni, and R. Settambolo Chirality 23 2011 730
    • (2011) Chirality , vol.23 , pp. 730
    • Lazzaroni, R.1    Settambolo, R.2
  • 23
    • 15944372237 scopus 로고    scopus 로고
    • Although no example of the photochemical Wolff rearrangement applied to the Arndt-Eistert reaction is described in the literature for an α,β-unsaturated diazoketone, a single example is described for the thermal rearrangement by Brueckner. However, the 2 diazoketones employed in this example are simple ones, containing no epimerizable stereocenters or heteroatoms in the chain. For this single example, see: T. Kapferer, R. Brueckner, A. Herzig, and W.A. Koenig Chem. Eur. J. 11 2005 2154
    • (2005) Chem. Eur. J. , vol.11 , pp. 2154
    • Kapferer, T.1    Brueckner, R.2    Herzig, A.3    Koenig, W.A.4


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.