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Volumn 55, Issue 22, 1999, Pages 6997-7010

An easy route to 11-hydroxy-eudesmanolides. Synthesis of (±) decipienin A

Author keywords

[No Author keywords available]

Indexed keywords

2 CYCLOHEXENONE DERIVATIVE; EUDESMANOLIDE DERIVATIVE; LITHIUM DERIVATIVE;

EID: 0033612101     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00328-2     Document Type: Article
Times cited : (23)

References (44)
  • 1
    • 0031979256 scopus 로고    scopus 로고
    • and references therein
    • a) Fraga, B.M. Nat. Prod. Reports, 1998, 15, 73 and references therein.
    • (1998) Nat. Prod. Reports , vol.15 , pp. 73
    • Fraga, B.M.1
  • 2
    • 0002058708 scopus 로고
    • The Biogenesis and Chemistry of Sesquiterpene Lactones
    • (Herz, W.; Grisebach, H. and Kirby, G. W. edts.), Springer-Verlag, New York
    • b) Fischer, N.H.; Olivier, E.J.; Fischer, H.D. "The Biogenesis and Chemistry of Sesquiterpene Lactones" in Fortschritte der Chemie Organischer Naturstoffe, Vol. 38, (Herz, W.; Grisebach, H. and Kirby, G. W. edts.), Springer-Verlag, New York, p. 47, 1979.
    • (1979) Fortschritte der Chemie Organischer Naturstoffe, , vol.38 , pp. 47
    • Fischer, N.H.1    Olivier, E.J.2    Fischer, H.D.3
  • 6
    • 0000760228 scopus 로고
    • Sesquiterpene lactones revisited: Recent developments in the assessment of biological activities and structure relationships
    • (Arnason, J.T.; Mata, R. and Romeo, J.T. eds.), Plenum Press, New York
    • f) Marles, R.J.; Pazos-Sanou, L.; Compadre, C.M.; Pezzuto, J.M.; Boszyk, E. and Arnason, J.T. "Sesquiterpene lactones revisited: Recent developments in the assessment of biological activities and structure relationships" in Phytochemistry of Medicinal Plants, Vol 29, (Arnason, J.T.; Mata, R. and Romeo, J.T. eds.), Plenum Press, New York, pp. 333-356, 1995.
    • (1995) Phytochemistry of Medicinal Plants , vol.29 , pp. 333-356
    • Marles, R.J.1    Pazos-Sanou, L.2    Compadre, C.M.3    Pezzuto, J.M.4    Boszyk, E.5    Arnason, J.T.6
  • 7
    • 0003847886 scopus 로고
    • New natural products and plant drugs with pharmacological, biological or therapeutical activity
    • (Wagner H. and Wolff, P. eds.), Springer Verlag, Berlin
    • a) Sticher, O. "New natural products and plant drugs with pharmacological, biological or therapeutical activity" in Proceedings of the First International Congress of Medicinal Plant Research. Section A" (Wagner H. and Wolff, P. eds.), Springer Verlag, Berlin, pp. 157-176, 1977.
    • (1977) Proceedings of the First International Congress of Medicinal Plant Research. Section A , pp. 157-176
    • Sticher, O.1
  • 24
    • 0013532668 scopus 로고    scopus 로고
    • note
    • The structure assigned by Kametani et al. in their original paper to compound 7 was the following: (Formula presented) When a mixture of 6 and 7 is treated with ethylene glycol, a single product is obtained. In the original paper, a wrong structure is proposed for this compound. (Formula presented) In fact, under these conditions, 8 also gives 9. (Formula presented)
  • 35
    • 0013521486 scopus 로고    scopus 로고
    • note
    • 3 was used: (Formula presented)
  • 43
    • 0032389691 scopus 로고    scopus 로고
    • This problem has been described by Greene et al. See ref. For a very powerful method of esterification of highly hindered alcohols see: Saitoh, K.; Shiina, I. and Mukaiyama, T. Chem. Lett. 1998, 679.
    • (1998) Chem. Lett. , pp. 679
    • Saitoh, K.1    Shiina, I.2    Mukaiyama, T.3
  • 44
    • 0013521487 scopus 로고    scopus 로고
    • note
    • The separation of the two epimers can be done more efficiently after reduction of the mixture of the epimers 10a and 10b and their subsequent oxidation to afford compound 10b and the lactone 14


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