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Volumn 73, Issue 3, 2008, Pages 1154-1157

A concise synthesis of lentiginosine derivatives using a pyridinium formation via the Mitsunobu reaction

Author keywords

[No Author keywords available]

Indexed keywords

LENTIGINOSINE; MITSUNOBU REACTION; PYRIDINIUM; STEREOISOMERS;

EID: 38849126849     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo702141b     Document Type: Article
Times cited : (42)

References (77)
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    • (2005) Curr. Org. Synth , vol.2 , pp. 39
    • Pyne, S.G.1
  • 21
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    • For reports of (±)-lentiginosine and its enantiomer syntheses that appeared after 2002, see: a
    • For reports of (±)-lentiginosine and its enantiomer syntheses that appeared after 2002, see: (a) Chen, M.-J.; Tsai, Y.-M. Tetrahedron Lett. 2007, 48, 6271.
    • (2007) Tetrahedron Lett , vol.48 , pp. 6271
    • Chen, M.-J.1    Tsai, Y.-M.2
  • 37
    • 38849130987 scopus 로고    scopus 로고
    • Both, )-lentiginosine and, -lentiginosine display selective inhibition for amyloglucosidases
    • Both (+)-lentiginosine and (-)-lentiginosine display selective inhibition for amyloglucosidases.
  • 61
    • 33746023969 scopus 로고    scopus 로고
    • For a recent example of displacement of activated alcohol by nucleophilic pyridine nitrogen under Mitsunobu conditions and further cyclization of N-Boc-protected 2-amino-6-propanol pyridine derivative, see: Lawton, G. R, Ji, H, Silverman, R. B. Tetrahedron Lett. 2006, 47, 6113
    • For a recent example of displacement of activated alcohol by nucleophilic pyridine nitrogen under Mitsunobu conditions and further cyclization of N-Boc-protected 2-amino-6-propanol pyridine derivative, see: Lawton, G. R.; Ji, H.; Silverman, R. B. Tetrahedron Lett. 2006, 47, 6113.
  • 62
    • 8444229667 scopus 로고    scopus 로고
    • For relevant examples, see: a
    • For relevant examples, see: (a) Gotchev, D.; Comins, D. L. Tetrahedron 2004, 60, 11751.
    • (2004) Tetrahedron , vol.60 , pp. 11751
    • Gotchev, D.1    Comins, D.L.2
  • 66
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    • The corresponding ketone was obtained in 88% yield by reacting 2-lithiopyridine with (R)-methyl-2,2-dimethyl-1,3-dioxolane-4- carboxylate.
    • (a) The corresponding ketone was obtained in 88% yield by reacting 2-lithiopyridine with (R)-methyl-2,2-dimethyl-1,3-dioxolane-4- carboxylate.
  • 69
    • 33749436403 scopus 로고    scopus 로고
    • For metal-catalyzed asymmetric hydrogenation of pyridine ring, see: b
    • For metal-catalyzed asymmetric hydrogenation of pyridine ring, see: (b) Lei, A.; Chen, M.; He, M.; Zhang, X. Eur. J. Org. Chem. 2006, 4343.
    • (2006) Eur. J. Org. Chem , pp. 4343
    • Lei, A.1    Chen, M.2    He, M.3    Zhang, X.4
  • 73
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    • For a review on asymmetric hydrogenation of heteroaromatic compounds, see: f, ASAP
    • For a review on asymmetric hydrogenation of heteroaromatic compounds, see: (f) Zhou, Y.-G. Acc. Chem. Res. 2007, ASAP.
    • (2007) Acc. Chem. Res
    • Zhou, Y.-G.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.