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Volumn 63, Issue 22, 1998, Pages 7628-7633

Studies relevant to ellagitannin chemistry: Highly diastereoselective intramolecular biaryl coupling in bis(iodotrimethoxybenzoyl) hexopyranose derivatives

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Indexed keywords


EID: 0000558904     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971722k     Document Type: Article
Times cited : (38)

References (37)
  • 11
    • 0027981393 scopus 로고
    • (b) Lipshutz, B. H.; Liu, Z.-P.; Kayser, F. Tetrahedron Lett. 1994, 35, 5567-5570. Examples of synthesis of ellagitannins by way of the diastereoselective esterification of glucose diols with racemic hexaalkoxydiphenoic acid derivatives have been very recently reported:
    • (1994) Tetrahedron Lett. , vol.35 , pp. 5567-5570
    • Lipshutz, B.H.1    Liu, Z.-P.2    Kayser, F.3
  • 15
    • 85034158982 scopus 로고    scopus 로고
    • note
    • 3.
  • 16
    • 0001073559 scopus 로고
    • General review on biaryl coupling: Sainsbury, M. Tetrahedron 1980, 36, 3327-3359.
    • (1980) Tetrahedron , vol.36 , pp. 3327-3359
    • Sainsbury, M.1
  • 23
    • 33947441668 scopus 로고
    • Fanta, P. E. Chem. Rev. 1946, 38, 139-196. Chem. Rev. 1964, 64, 613-632. Synthesis 1974, 9-21.
    • (1946) Chem. Rev. , vol.38 , pp. 139-196
    • Fanta, P.E.1
  • 26
    • 85034168906 scopus 로고    scopus 로고
    • Despite the high temperature used, the reactions were clean, and the conversion was essentially quantitative
    • Despite the high temperature used, the reactions were clean, and the conversion was essentially quantitative.
  • 27
    • 0000420442 scopus 로고
    • Okuda, T.; Yoshida, T.; Hatano, T.; Koga, T.; Toh, N.; Kuriyama, K. Tetrahedron Lett. 1982, 23, 3937-3940; 3941-3944. For comparative results, see Table 2. A negative Cotton effect at about 250 nm followed by a positive Cotton effect at about 225 nm was taken as evidence for the (S)-configuation of the hexamethoxydiphenoyl unit.
    • (1982) Tetrahedron Lett. , vol.23 , pp. 3937-3940
    • Okuda, T.1    Yoshida, T.2    Hatano, T.3    Koga, T.4    Toh, N.5    Kuriyama, K.6
  • 28
    • 85034191685 scopus 로고    scopus 로고
    • The ratio of products was improved to 4:1:1 when the reaction was performed at lower temperature (105 °C, 5 d).
    • The ratio of products was improved to 4:1:1 when the reaction was performed at lower temperature (105 °C, 5 d).
  • 31
    • 85034188696 scopus 로고    scopus 로고
    • The (R)-atropisomer is generated in this system if one of the benzoyl groups is in the (E)-syn conformation.
    • The (R)-atropisomer is generated in this system if one of the benzoyl groups is in the (E)-syn conformation.
  • 37
    • 85034177643 scopus 로고    scopus 로고
    • note
    • Data for the reduced products, 4, 8b, 11, and 14, are provided in Supporting Information.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.