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Volumn 69, Issue 12, 2004, Pages 4116-4125

Synthesis of optically pure (+)-puraquinonic acid and assignment of absolute configuration to natural (-)-puraquinonic acid. Use of radical cyclization for asymmetric generation of a quaternary center

Author keywords

[No Author keywords available]

Indexed keywords

ALCOHOLS; ALDEHYDES; AROMATIC COMPOUNDS; DEGRADATION; SYNTHESIS (CHEMICAL);

EID: 2942567915     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo040115b     Document Type: Article
Times cited : (33)

References (51)
  • 2
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    • Illudalanes have the skeleton (i): (a) Ayer, W. A.; Browne, L. M. Tetrahedron 1981, 37, 2199-2248.
    • (1981) Tetrahedron , vol.37 , pp. 2199-2248
    • Ayer, W.A.1    Browne, L.M.2
  • 6
    • 0000552684 scopus 로고    scopus 로고
    • Yarnold, J. R., Stratton, M. R., McMillan, T. J., Eds.; Chapman and Hall: London
    • (c) Mason, M. D. In Molecular Biology for Oncologists; Yarnold, J. R., Stratton, M. R., McMillan, T. J., Eds.; Chapman and Hall: London, 1996; pp 112-121.
    • (1996) Molecular Biology for Oncologists , pp. 112-121
    • Mason, M.D.1
  • 11
    • 0035903967 scopus 로고    scopus 로고
    • Synthesis of (±)-deliquinone and (±)-puraquinonic acid ethyl ester: Kraus, G. A.; Choudhury, P. K. Tetrahedron Lett. 2001, 42, 6649-6650.
    • (2001) Tetrahedron Lett. , vol.42 , pp. 6649-6650
    • Kraus, G.A.1    Choudhury, P.K.2
  • 12
    • 0000449913 scopus 로고
    • Construction of quaternary centers: (a) Martin, S. F. Tetrahedron 1980, 36, 419-460.
    • (1980) Tetrahedron , vol.36 , pp. 419-460
    • Martin, S.F.1
  • 13
    • 0001521888 scopus 로고
    • (b) Fuji, K. Chem. Rev. 1993, 93, 2037-2066.
    • (1993) Chem. Rev. , vol.93 , pp. 2037-2066
    • Fuji, K.1
  • 19
    • 0037427250 scopus 로고    scopus 로고
    • and references therein
    • Compare: Mermerian, A. H.; Fu, G. C. J. Am. Chem. Soc. 2003, 125, 4050-4051 and references therein.
    • (2003) J. Am. Chem. Soc. , vol.125 , pp. 4050-4051
    • Mermerian, A.H.1    Fu, G.C.2
  • 26
    • 2942613907 scopus 로고    scopus 로고
    • note
    • 4, 68%), and treatment with DBU then gave 17: [Diagram presented]
  • 30
    • 2942619159 scopus 로고    scopus 로고
    • note
    • 3, the allylic alcohol (69%) was racemic.
  • 31
    • 2942622733 scopus 로고    scopus 로고
    • note
    • Made from 2,5-dimethylphenol by the method of ref 22, except that the formyl group was best generated by benzylic bromination,23 followed by oxidation with DMSO (see ref 24 and Supporting Information).
  • 44
    • 2942562918 scopus 로고    scopus 로고
    • note
    • We tried Schrock's catalyst (2,6-diisopropylphenylimidoneophylidene molybdenum(VI) bis(hexafluoro)-tert-butoxide) and Grubbs' first generation catalyst (bis(tricyclohexylphosphine)benzylidene ruthenium(IV) dichloride).
  • 45
    • 2942526022 scopus 로고    scopus 로고
    • note
    • 2O; 90%) of the ketone corresponding to 40. We thank S. Hisaindee of this laboratory for a sample of the ketone.
  • 47
    • 0000584420 scopus 로고
    • Morrison, J. D., Ed.; Academic Press: Orlando, FL
    • Heathcock, C. H. In Asymmetric Synthesis; Morrison, J. D., Ed.; Academic Press: Orlando, FL, 1984; Vol. 3, pp 111-212.
    • (1984) Asymmetric Synthesis , vol.3 , pp. 111-212
    • Heathcock, C.H.1
  • 48
    • 0037121776 scopus 로고    scopus 로고
    • For another example where this method was the best of several we tried, see: Clive, D. L. J.; Huang, X. Tetrahedron 2002, 58, 10243-10250.
    • (2002) Tetrahedron , vol.58 , pp. 10243-10250
    • Clive, D.L.J.1    Huang, X.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.