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Volumn 62, Issue 8, 1997, Pages 2344-2349

Total synthesis of neohedycaryol. Its possible role in the biosynthesis of eudesmane sesquiterpenes

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA EUDESMOL; BETA EUDESMOL; GAMMA EUDESMOL; NEOHEDYCARYOL; SESQUITERPENE; UNCLASSIFIED DRUG;

EID: 0031001877     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo962056a     Document Type: Article
Times cited : (15)

References (55)
  • 1
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    • The numbering system as given in structure 1 will be followed throughout the text of this paper
    • The numbering system as given in structure 1 will be followed throughout the text of this paper.
  • 9
    • 0004205843 scopus 로고
    • Chapman & Hall: London, Mono- and Sesquiterpenoids
    • (a) Connolly, J. D.; Hill, R. A. Dictionary of Terpenoids; Chapman & Hall: London, 1991; Vol. 1, Mono- and Sesquiterpenoids.
    • (1991) Dictionary of Terpenoids , vol.1
    • Connolly, J.D.1    Hill, R.A.2
  • 17
    • 0000992524 scopus 로고
    • An indication for this pathway is the cooccurrence of trans,cis-farnesol (a precursor of cis,trans-germacranes) and epi-eudesmanes in Galbanum species, see: Thomas, A. F.; Ozainne, M. Helv. Chim. Acta 1978, 61, 2874.
    • (1978) Helv. Chim. Acta , vol.61 , pp. 2874
    • Thomas, A.F.1    Ozainne, M.2
  • 19
    • 0013500096 scopus 로고
    • All trans,cis-germacranes (heliangolides) and cis,trans-germacranes (melampolides) possess one or more lactone rings, an exception being helminthogermacrene, see: Winter, R. E. K.; Dorn, F.; Arigoni, D. J. Org. Chem. 1980, 45, 4786.
    • (1980) J. Org. Chem. , vol.45 , pp. 4786
    • Winter, R.E.K.1    Dorn, F.2    Arigoni, D.3
  • 24
    • 0004138326 scopus 로고
    • The sesquiterpenes
    • Newman, A. A., Ed.; Academic Press: London
    • (b) Roberts, J. S. The sesquiterpenes. In Chemistry of Terpenes and terpenoids; Newman, A. A., Ed.; Academic Press: London, 1972; pp 88-146.
    • (1972) Chemistry of Terpenes and Terpenoids , pp. 88-146
    • Roberts, J.S.1
  • 30
    • 8244245641 scopus 로고    scopus 로고
    • Only the interconversion of the conformations by rotation of the double bonds is considered
    • Only the interconversion of the conformations by rotation of the double bonds is considered.
  • 36
    • 0028232283 scopus 로고
    • For some recent examples in germacrane chemistry, see: (b) Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. Tetrahedron 1994, 50, 4755, and (c) Zhabinskii, V. A.; Minnaard, A. J.; Wijnberg, J. B. P. A.; de Groot, A. J. Org. Chem. 1996, 61, 4022.
    • (1994) Tetrahedron , vol.50 , pp. 4755
    • Minnaard, A.J.1    Wijnberg, J.B.P.A.2    De Groot, A.3
  • 37
  • 43
    • 8244246993 scopus 로고    scopus 로고
    • note
    • +, 9), 240 (33), 238 (100), 225 (7), 223 (21), 197 (20), 195 (60), 187 (34), 159 (36), 59 (48).
  • 45
    • 0011442739 scopus 로고
    • Initially, it was thought that just the presence of the homoallylic double bond frustrated the mesylation of 11, see: Shoppee, C. W.; Summers, G. H. R. J. Chem. Soc. 1952, 3361.
    • (1952) J. Chem. Soc. , pp. 3361
    • Shoppee, C.W.1    Summers, G.H.R.2
  • 50
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    • Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, Chapter 3 and references cited therein
    • Paddon-Row, M. N.; Jordan, K. D. In Modern Models of Bonding and Delocalization; Liebman, J. F., Greenberg, A., Eds.; VCH Publishers: New York, 1988, Chapter 3 and references cited therein.
    • (1988) Modern Models of Bonding and Delocalization
    • Paddon-Row, M.N.1    Jordan, K.D.2
  • 54
    • 8244250014 scopus 로고    scopus 로고
    • GC analysis revealed the presence of a small amount (< 10%) of another compound, probably a double bond isomer of 10
    • GC analysis revealed the presence of a small amount (< 10%) of another compound, probably a double bond isomer of 10.
  • 55
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    • Reference 8, van Beek et al.
    • Beek, V.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.