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Volumn 7, Issue 14, 2005, Pages 2949-2952

Ring expansion of azetidinium ylides: Rapid access to the pyrrolizidine alkaloids turneforcidine and platynecine

Author keywords

[No Author keywords available]

Indexed keywords

AZETIDINE DERIVATIVE; FUSED HETEROCYCLIC RINGS; PLATYNECINE; PYRROLIZIDINE ALKALOID; TURNEFORCIDINE;

EID: 22244445827     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol050915o     Document Type: Article
Times cited : (68)

References (61)
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    • For a recent report that suggests an alternative ion-pair-mediated mechanism, see: Hanessian, S.; Mauduit, M. Angew. Chem., Int. Ed. 2001, 40, 3810-3813.
    • (2001) Angew. Chem., Int. Ed. , vol.40 , pp. 3810-3813
    • Hanessian, S.1    Mauduit, M.2
  • 25
    • 0035861622 scopus 로고    scopus 로고
    • Previous syntheses of turneforcidine: (a) Wee, A. G. H. J. Org. Chem. 2001, 66, 8513-8517.
    • (2001) J. Org. Chem. , vol.66 , pp. 8513-8517
    • Wee, A.G.H.1
  • 39
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    • See also refs 8c, 8e, and 8f
    • (g) Rueger, H.; Benn, M. Heterocycles 1983, 1331-1334. See also refs 8c, 8e, and 8f.
    • (1983) Heterocycles , pp. 1331-1334
    • Rueger, H.1    Benn, M.2
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    • see refs 8c, 8e, and 8f
    • For previous preparation of 3a and/or 4a, see refs 8c, 8e, and 8f.
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    • Naidu, B.N.1
  • 44
    • 0037017775 scopus 로고    scopus 로고
    • For related observations involving oxonium ylide [1,2]- and [2,3]-shifts, see: (a) Marmsäter, F. P.; Vanecko, J. A.; West, F. G. Tetrahedron 2002, 58, 2027-2040.
    • (2002) Tetrahedron , vol.58 , pp. 2027-2040
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  • 51
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    • See refs 6a and 6d
    • Complete preference for benzylic migration in ring expansion of morpholinium ylides has also been noted. See refs 6a and 6d.
  • 52
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    • Kim, S.1    Yoon, J.-Y.2
  • 60
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    • see ref 13
    • However, epimerization of the initial product mixture could be effected via slow elution through a silica gel column using a less polar eluant to furnish 3a + 4a in a 94:6 ratio. For n related example, see ref 13.
  • 61
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    • Saba and co-workers have recently reported a similar approach to indolizidines using doubly stabilized metallocarbene intermediates: Muroni, D.; Saba, A.; Culeddu, N. Tetrahedron: Asymmetry 2004, 15, 2609-2614.
    • (2004) Tetrahedron: Asymmetry , vol.15 , pp. 2609-2614
    • Muroni, D.1    Saba, A.2    Culeddu, N.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.