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Volumn 45, Issue 39, 2006, Pages 6532-6535

Total synthesis and absolute stereochemistry of polygalolides A and B

Author keywords

Aldol reaction; Carbonyl ylides; Cycloaddition; Diazo compounds; Total synthesis

Indexed keywords

ALDOL REACTIONS; CORE STRUCTURE; CYCLOADDITION; DIAZO COMPOUNDS; POLYGALOLIDES; TOTAL SYNTHESIS;

EID: 33749856973     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/anie.200602030     Document Type: Article
Times cited : (68)

References (38)
  • 6
    • 0027941935 scopus 로고
    • For recent studies on the synthesis of bioactive molecules using a carbonyl ylide cycloaddition strategy, see: a) H. Koyama, R. G. Ball, G. D. Berger, Tetrahedron Lett. 1994, 35, 9185-9188;
    • (1994) Tetrahedron Lett. , vol.35 , pp. 9185-9188
    • Koyama, H.1    Ball, R.G.2    Berger, G.D.3
  • 15
    • 0344875710 scopus 로고    scopus 로고
    • Angew. Chem. Int. Ed. 2003, 42, 5351-5355;
    • (2003) Angew. Chem. Int. Ed. , vol.42 , pp. 5351-5355
  • 20
    • 33749869983 scopus 로고    scopus 로고
    • W. E. Bauta et al., see Supporting Information
    • c) W. E. Bauta et al., see Supporting Information;
  • 28
    • 33749836515 scopus 로고    scopus 로고
    • note
    • The homochirality of ketone 7 and cycloadduct 3 was confirmed by HPLC on a chiral stationary phase.
  • 29
    • 0010497656 scopus 로고
    • W. J. Elliott, J. Fried, J. Org. Chem. 1978, 43, 2708-2710. We thank a referee for bringing the reference to our attention.
    • (1978) J. Org. Chem. , vol.43 , pp. 2708-2710
    • Elliott, W.J.1    Fried, J.2
  • 30
    • 33749871372 scopus 로고    scopus 로고
    • note
    • 4 at room temperature to provide a 1:1 mixture of diastereomeric cycloadducts in 35 % yield, indicating that carbonyl ylide 5 was formed under these conditions. Heating is required to promote the intramolecular cycloaddition with a nonactivated alkene.
  • 31
    • 33749822413 scopus 로고    scopus 로고
    • note
    • 4 (41%).
  • 33
    • 33749861664 scopus 로고    scopus 로고
    • note
    • The cycloaddition is not scale dependent and the cycloadduct 3 was obtained in 70% yield when the reaction was performed on a 500-mg scale.
  • 38
    • 33749864724 scopus 로고    scopus 로고
    • note
    • A plausible biogenesis of polygalolides is illustrated schematically below. (Chemical Equation Presented)


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.