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Volumn 67, Issue 26, 2002, Pages 9443-9448

Diastereoselective total synthesis of both enantiomers of epolactaene

Author keywords

[No Author keywords available]

Indexed keywords

HYDROLYSIS; SILICA GEL; SYNTHESIS (CHEMICAL);

EID: 0037184834     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo025641m     Document Type: Article
Times cited : (41)

References (31)
  • 12
    • 0033522980 scopus 로고    scopus 로고
    • Marumoto, S.; Kogen. H.; Naruto, S. J. Org. Chem. 1998, 63, 2068. Tetrahedron 1999, 55, 7129, 7145.
    • (1999) Tetrahedron , vol.55 , pp. 7129
  • 14
    • 0347781397 scopus 로고
    • For reviews, see: Jones, G. Org. React. (N.Y.) 1967, 15, 204. Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; Trost, B. M., Editor-in-Chief; Pergamon Press: Oxford, 1991; Vol. 2, p 341.
    • (1967) Org. React. (N.Y.) , vol.15 , pp. 204
    • Jones, G.1
  • 15
    • 0000201762 scopus 로고
    • Trost, B. M., Editor-in-Chief; Pergamon Press: Oxford
    • For reviews, see: Jones, G. Org. React. (N.Y.) 1967, 15, 204. Tietze, L. F.; Beifuss, U. In Comprehensive Organic Synthesis; Trost, B. M., Editor-in-Chief; Pergamon Press: Oxford, 1991; Vol. 2, p 341.
    • (1991) Comprehensive Organic Synthesis , vol.2 , pp. 341
    • Tietze, L.F.1    Beifuss, U.2
  • 19
    • 12244294425 scopus 로고    scopus 로고
    • note
    • Because of the instability of the condensation products, rough purification was performed by rapid column chromatography on florisil gel.
  • 20
    • 12244267918 scopus 로고    scopus 로고
    • note
    • The Knoevenagel reaction of β-ketonitrile 13c with benzaldehyde and isobutyraldehyde afforded E-olefins selectively in 89% and 95% yields, respectively.
  • 22
    • 12244262191 scopus 로고
    • and references therein
    • 4-mediated hydration of nitriles has been reported to proceed under neutral conditions at 120 °C, but our nitrile 16 was decomposed under the literature conditions. Murahashi, S.; Sasao, S.; Saito, E.; Naota, T. J. Am. Chem. Soc. 1992, 57, 2521 and references therein.
    • (1992) J. Am. Chem. Soc. , vol.57 , pp. 2521
    • Murahashi, S.1    Sasao, S.2    Saito, E.3    Naota, T.4
  • 24
    • 12244288257 scopus 로고    scopus 로고
    • note
    • The stereochemistry of epoxyhydrofuran 20 was not determined.
  • 26
    • 12244279896 scopus 로고    scopus 로고
    • note
    • 8
  • 27
    • 12244308989 scopus 로고    scopus 로고
    • note
    • 8
  • 29
    • 12244306853 scopus 로고    scopus 로고
    • note
    • A probable mechanism for the Knoevenagel reaction is as follows: an ammonium salt reacts with an aldehyde to afford an imine, which then reacts with a nucleophile. The isomerization of imine and enamine is a well-known process, which leads to the racemic imine. For the above reaction mechanism, see the reviews in ref 11.
  • 31
    • 33947085552 scopus 로고
    • Dale, J. A.; Dull, D. L.; Mosher, H. S. J. Org. Chem. 1969, 34, 2543. Dale, J. A.; Mosher, H. S. J. Am. Chem. Soc. 1973, 95, 512.
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 512
    • Dale, J.A.1    Mosher, H.S.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.