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Volumn 10, Issue 3, 2008, Pages 413-416

A non-diels-alder approach to the cis-decalin core of branimycin

Author keywords

[No Author keywords available]

Indexed keywords

BRANIMYCIN; COPPER; CYCLOALKANE DERIVATIVE; DECALIN; MACROLIDE; NAPHTHALENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 38949125436     PISSN: 15237060     EISSN: None     Source Type: Journal    
DOI: 10.1021/ol7027338     Document Type: Article
Times cited : (13)

References (37)
  • 15
  • 19
    • 0037239379 scopus 로고    scopus 로고
    • For other examples of transition metal-catalyzed opening of oxabicyclic alkenes see: a
    • For other examples of transition metal-catalyzed opening of oxabicyclic alkenes see: (a) Lautens, M.; Fagnou, K.; Hiebert, S. Acc. Chem. Res. 2003, 36, 48-58.
    • (2003) Acc. Chem. Res , vol.36 , pp. 48-58
    • Lautens, M.1    Fagnou, K.2    Hiebert, S.3
  • 20
    • 1042288169 scopus 로고    scopus 로고
    • and references therein
    • (b) Lautens, M.; Hiebert, S. J. Am. Chem. Soc. 2004, 126, 1437-1447 and references therein.
    • (2004) J. Am. Chem. Soc , vol.126 , pp. 1437-1447
    • Lautens, M.1    Hiebert, S.2
  • 27
    • 38949125779 scopus 로고    scopus 로고
    • The side product of the reaction (25%) is compound 9a. Figure Presented Conversion of 9a under acidic conditions improved the yield of the desired acetal to 88%.
    • The side product of the reaction (25%) is compound 9a. Figure Presented Conversion of 9a under acidic conditions improved the yield of the desired acetal to 88%.
  • 28
    • 1842461758 scopus 로고    scopus 로고
    • Takeda, T, Ed, Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim
    • Takeda, T., Ed. Modern Carbonyl Olefination; Wiley-VCH Verlag GmbH & Co. KGaA: Weinheim, 2004.
    • (2004) Modern Carbonyl Olefination
  • 37
    • 38949182947 scopus 로고    scopus 로고
    • It has to be pointed out that, although the RCM reaction was quantitative, attempts to subject compounds 19 and 20 to chromatography in the presence of air resulted in a substantial loss of the material, most probably via oxidation of the diene system. For example, exposure of structurally similar compound A to air gave after 20 min hydroperoxide B in 90% yield. Gromov, A. Ph.D. Thesis in preparation. Figure Presented
    • It has to be pointed out that, although the RCM reaction was quantitative, attempts to subject compounds 19 and 20 to chromatography in the presence of air resulted in a substantial loss of the material, most probably via oxidation of the diene system. For example, exposure of structurally similar compound A to air gave after 20 min hydroperoxide B in 90% yield. Gromov, A. Ph.D. Thesis in preparation. Figure Presented


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.