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Volumn 61, Issue 20, 1996, Pages 6922-6930

Stereoselective syntheses of cis- and trans-isomers of α-hydroxy-α,β-dibenzyl-γ-butyrolactone lignans: New syntheses of (±)-trachelogenin and (±)-guayadequiol

Author keywords

[No Author keywords available]

Indexed keywords

GAMMA BUTYROLACTONE DERIVATIVE; GUAYADEQUIOL; LIGNAN; TRACHELOGENIN; UNCLASSIFIED DRUG;

EID: 0029801091     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo9601932     Document Type: Article
Times cited : (38)

References (49)
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  • 2
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  • 12
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    • and references cited within
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    • For preliminary communications, see: (a) Moritani, Y.; Ukita, T.; Nishitani, T.; Seki, M.; Iwasaki, T. Tetrahedron Lett. 1990, 31, 3615. (b) Moritani, Y.; Fukushima, C.; Ogiku, T., Ukita, T.; Miyagishima, T.; Iwasaki, T. Tetrahedron Lett. 1993, 34, 2787.
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  • 28
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    • note
    • Similar results were obtained when we calculated the heats of formation of the transition structure in the electrophilic addition of methyl iodide to the enolates of dibenzyl lactone using the AM1 or PM3 program.
  • 36
    • 0026637882 scopus 로고    scopus 로고
    • Ogiku, T.; Yoshida, S.; Takahashi, M.; Kuroda, T.; Ohmizu, H.; Iwasaki, T. Tetrahedron Lett. 1992, 33, 4473; 33, 4477.
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    • note
    • 1H NMR (NOE).
  • 38
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    • note
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  • 39
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    • Deuteriation probably takes place first on oxygen and the stereochemistry-determining step is the second deuteriation on carbon; Fleming, I.; Lewis, J. J. J. Chem. Soc., Chem. Commun. 1985, 149.
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  • 40
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    • note
    • Brown et al. reported the hydroxylation of the enolate of 1l-o with molecular hydrogen. However, the diastereoselectivity was not observed in this reaction, see ref 2c.
  • 42
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    • note
    • The NMR spectra of the products (1a, 2c) obtained here were completely consistent with those of (±)-trachelogenin and (±)-guayadequiol reported in refs 1-3.
  • 43
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    • note
    • 1H NMR.
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    • 1H NMR.
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    • 1H NME (NOE).
  • 46
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    • note
    • 1H NMR.
  • 47
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    • TRIPOS, Inc., 1699 S. Hanley Road, St. Louis, MO 63144-2913
    • TRIPOS, Inc., 1699 S. Hanley Road, St. Louis, MO 63144-2913.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.