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Volumn 38, Issue 5, 1999, Pages 683-686

Asymmetric total synthesis of fredericamycin A

Author keywords

Antitumor agents; Asymmetric synthesis; Cycloadditions; Natural products rearrangements; Total synthesis

Indexed keywords

ACID ANHYDRIDE; FREDERICAMYCIN A;

EID: 0033105733     PISSN: 14337851     EISSN: None     Source Type: Journal    
DOI: 10.1002/(SICI)1521-3773(19990301)38:5<683::AID-ANIE683>3.0.CO;2-0     Document Type: Article
Times cited : (63)

References (48)
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    • We are also investigating a different approach to the total synthesis of 1 based on an intramolecular [4+2] cycloaddition: see a) Y. Kita, R. Okunaka, T. Honda, M. Shindo, O. Tamura, Tetrahedron Lett. 1989, 30, 3995-3998;
    • (1989) Tetrahedron Lett. , vol.30 , pp. 3995-3998
    • Kita, Y.1    Okunaka, R.2    Honda, T.3    Shindo, M.4    Tamura, O.5
  • 23
    • 0024538538 scopus 로고
    • A similar intramolecular strategy was reported separately: see e) M. Toyota, S. Terashima, Terahedron Lett. 1989, 30, 829-832.
    • (1989) Terahedron Lett. , vol.30 , pp. 829-832
    • Toyota, M.1    Terashima, S.2
  • 24
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    • For a study on construction of optically active quaternary carbon in connection with 1: see W. Trypke, A. Steigel, M. Braun, Synlett 1992, 827-829.
    • (1992) Synlett , pp. 827-829
    • Trypke, W.1    Steigel, A.2    Braun, M.3
  • 28
    • 85004434450 scopus 로고
    • Application of this method to the total syntheses of peri-hydroxy polyaromatic compounds: see reviews, a) Y. Tamura, Y. Kita, Yuki Gosei Kagaku Kyokaishi 1988, 46, 205-217
    • (1988) Yuki Gosei Kagaku Kyokaishi , vol.46 , pp. 205-217
    • Tamura, Y.1    Kita, Y.2
  • 29
    • 25044457013 scopus 로고
    • [Chem. Abstr. 1988, 109, 129465d];
    • (1988) Chem. Abstr. , vol.109
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    • 4243984376 scopus 로고    scopus 로고
    • [Chem. Abstr. 1997, 127, 190540n];
    • (1997) Chem. Abstr. , vol.127
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    • 33747531180 scopus 로고    scopus 로고
    • note
    • The enone 3 was obtained from methyl 2-methoxy-4,6-dimethylpyridine-3-carboxylate as per Scheme 5. The details will be presented in the forthcoming full paper. (Chemical Equation Presented) Scheme 5. Synthesis of 3.
  • 42
    • 33747550049 scopus 로고    scopus 로고
    • note
    • Optical purities of the intermediates (5, 6, and 9) were determined by HPLC using Daicel CHIRALCEL OD (n-hexane-iPrOH), and those of 2, 7, 8, (R)- and (S)-14, and (S)-15 by Daicel CHIRALPAK AD (n-hexane-iPrOH).
  • 43
    • 33747531839 scopus 로고    scopus 로고
    • note
    • Crystallographic data (excluding structure factors) for the structures reported in this paper have been deposited with the Cambridge Crystallographic Data Center as supplementary publication no. CCDC-102892 (for (-)-2), CCDC-102893 (for (+)-7), and CCDC-102894 {for methyl 2-methoxy-2-[3,4,6-trimethoxy-2-(methoxycarbonyl)phenyl]acetate, a precursor of 13}. Copies of the data can be obtained free of charge on application to CCDC, 12 Union Road, Cambridge CB2 1EZ, UK (fax: (+44)1223-336-033; e-mail: deposit@ccdc.cam.ac.uk).
  • 44
    • 33747574646 scopus 로고    scopus 로고
    • note
    • [11c]
  • 48
    • 33747535905 scopus 로고    scopus 로고
    • note
    • 3COOH.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.