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Volumn , Issue 22, 1999, Pages 3315-3321

A formal synthesis of (+)-pyripyropene A using a biomimetic epoxy-olefin cyclisation: Effect of epoxy alcohol/ether on cyclisation efficiency

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EID: 2342526653     PISSN: 0300922X     EISSN: None     Source Type: Journal    
DOI: 10.1039/a906589j     Document Type: Article
Times cited : (14)

References (33)
  • 27
    • 33747029733 scopus 로고    scopus 로고
    • note
    • It was important to reduce the amount of allylic chloride present in the reaction mixture as it was found to be inefficient in the subsequent alkylation reaction.
  • 28
    • 0001428613 scopus 로고
    • 5) resulted in lower yields of the allylic bromide 21 and led to bromohydrin formation. 20 β-Keto esters are known to cyclise through oxygen rather than carbon, see: T. R. Hoye, A. J. Caruso and M. J. Kurth, J. Org. Chem., 1981, 46, 3550;
    • (1981) J. Org. Chem. , vol.46 , pp. 3550
    • Hoye, T.R.1    Caruso, A.J.2    Kurth, M.J.3
  • 30
    • 33747016195 scopus 로고    scopus 로고
    • note
    • From molecular modelling (SPARTAN) it was found that 27 was lower in energy than the conjugated tetrasubstituted double bond isomer 2.
  • 31
    • 33747022246 scopus 로고    scopus 로고
    • 13C NMR, mass and IR analyses
    • 13C NMR, mass and IR analyses.
  • 32
    • 33746982868 scopus 로고    scopus 로고
    • note
    • The recovered isomer 28 was enriched in one diastereomer after 2 h reflux with NaH. After 4 h reflux, the recovered isomer 28 appeared to be one diastereomer only, suggesting a difference in deprotonation rates for the two diastereomeric esters.


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.