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Volumn 9, Issue 16, 2007, Pages 3001-3004

Synthesis of the C3-C18 fragment of amphidinolides G and H

Author keywords

[No Author keywords available]

Indexed keywords

AMPHIDINOLIDE G; AMPHIDINOLIDE H; MACROLIDE; UNCLASSIFIED DRUG;

EID: 34547936956     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol071024e     Document Type: Article
Times cited : (25)

References (47)
  • 11
    • 0032532231 scopus 로고    scopus 로고
    • Amphidinolide H: (a) Chakraborty, T. K.; Suresh, V. R. Tetrahedron Lett. 1998, 39, 7775.
    • Amphidinolide H: (a) Chakraborty, T. K.; Suresh, V. R. Tetrahedron Lett. 1998, 39, 7775.
  • 17
    • 0031536796 scopus 로고    scopus 로고
    • For representative papers regarding synthetic work on amphidinolide B, see: a
    • For representative papers regarding synthetic work on amphidinolide B, see: (a) Chakraborty, T. K.; Suresh, V. S. Chem. Lett. 1997, 6, 565.
    • (1997) Chem. Lett , vol.6 , pp. 565
    • Chakraborty, T.K.1    Suresh, V.S.2
  • 31
    • 34547929867 scopus 로고    scopus 로고
    • Other conditions explored were PPh3/I2/imidazole; PPh3/CI4; NaI/ heat; and MsCl/NaI.
    • Other conditions explored were PPh3/I2/imidazole; PPh3/CI4; NaI/ heat; and MsCl/NaI.
  • 35
    • 34547935703 scopus 로고    scopus 로고
    • The enantiomeric excess of this reaction was determined by Mosher ester analysis of the α-hydroxyester 18
    • The enantiomeric excess of this reaction was determined by Mosher ester analysis of the α-hydroxyester 18.
  • 42
    • 34547960669 scopus 로고    scopus 로고
    • The yield of alkyllithium species 20 was determined by trapping 20 with amide 5 and isolation of the ketone 21 thus formed.
    • The yield of alkyllithium species 20 was determined by trapping 20 with amide 5 and isolation of the ketone 21 thus formed.
  • 43
    • 34547939068 scopus 로고    scopus 로고
    • For reviews about the cyclization of usaturated organolithiums, see: a, Pergamon Press: New York, New York
    • For reviews about the cyclization of usaturated organolithiums, see: (a) Clayden, J. Organolithiums: Selectivity for Synthesis; Pergamon Press: New York, New York, 2002; Vol. 3, pp 293-335.
    • (2002) Organolithiums: Selectivity for Synthesis , vol.3 , pp. 293-335
    • Clayden, J.1
  • 46
    • 34547948111 scopus 로고    scopus 로고
    • Because the amide 5 had an ee of 80%, the coupling yielded ∼10% of the (8R)-epimer of ketone 21, which could be separated by column chromatography at this stage.
    • Because the amide 5 had an ee of 80%, the coupling yielded ∼10% of the (8R)-epimer of ketone 21, which could be separated by column chromatography at this stage.
  • 47
    • 34547941012 scopus 로고    scopus 로고
    • The relative stereochemistry was confirmed after converting the alcohol into an acetonide by NOESY NMR spectroscopy see Supporting Information
    • The relative stereochemistry was confirmed after converting the alcohol into an acetonide by NOESY NMR spectroscopy (see Supporting Information).


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.