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Volumn 55, Issue 8, 1999, Pages 2115-2146

The synthesis of germacrane sesquiterpenes and related compounds

Author keywords

[No Author keywords available]

Indexed keywords

CARBON; GERMACRANE DERIVATIVE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0033582442     PISSN: 00404020     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0040-4020(99)00025-3     Document Type: Review
Times cited : (45)

References (194)
  • 1
    • 0004205843 scopus 로고
    • Mono- and Sesquiterpenoids. London: Chapman & Hall
    • Connolly JD, Hill RA. Dictionary of Terpenoids; Vol. 1, Mono- and Sesquiterpenoids. London: Chapman & Hall, 1991:214-285.
    • (1991) Dictionary of Terpenoids , vol.1 , pp. 214-285
    • Connolly, J.D.1    Hill, R.A.2
  • 2
    • 84987306140 scopus 로고
    • For an extensive review, see: Herz W. Israel J. Chem. 1977;16:32-44.
    • (1977) Israel J. Chem. , vol.16 , pp. 32-44
    • Herz, W.1
  • 3
    • 37049115186 scopus 로고
    • The suffix "olide", as in "germacranolide" is used to indicate the presence of a lactone group
    • The conventions proposed for describing germacrane sesquiterpenes are followed, see: Rogers D, Moss GP, Neidle S. J. Chem. Soc., Chem. Comm. 1972:142-143. The suffix "olide", as in "germacranolide" is used to indicate the presence of a lactone group.
    • (1972) J. Chem. Soc., Chem. Comm. , pp. 142-143
    • Rogers, D.1    Moss, G.P.2    Neidle, S.3
  • 4
    • 0000028063 scopus 로고
    • For some representative examples, see: (a) Sutherland JK. Tetrahedron 1974;30:1651-1660.
    • (1974) Tetrahedron , vol.30 , pp. 1651-1660
    • Sutherland, J.K.1
  • 5
  • 7
    • 0001320913 scopus 로고
    • During the rotation of a double bond, the vinylic hydrogen passes through the center of the ring (jump-rope rotation), see: Marshall JA, Audia VH, Jenson TM, Guida WC. Tetrahedron 1986;42:1703-1709.
    • (1986) Tetrahedron , vol.42 , pp. 1703-1709
    • Marshall, J.A.1    Audia, V.H.2    Jenson, T.M.3    Guida, W.C.4
  • 10
    • 0013561142 scopus 로고    scopus 로고
    • Unpublished results from this laboratory. See also reference 6
    • Unpublished results from this laboratory. See also reference 6.
  • 15
    • 0000951088 scopus 로고
    • Sesquiterpene lactones: Biogenesis and biomimetic transformations
    • Towers GHN, Stafford HA, editors: Biochemistry of the Mevalonic Acid Pathway to Terpenoids New York: Plenum Press and references cited therein
    • Fischer NH. Sesquiterpene lactones: Biogenesis and biomimetic transformations. In: Towers GHN, Stafford HA, editors. Recent Advances in Phytochemistry, Vol. 24: Biochemistry of the Mevalonic Acid Pathway to Terpenoids. New York: Plenum Press, 1990:161-201 and references cited therein.
    • (1990) Recent Advances in Phytochemistry , vol.24 , pp. 161-201
    • Fischer, N.H.1
  • 23
    • 0013523461 scopus 로고    scopus 로고
    • Germacranes readily undergo Cope rearrangement to elernanes, see subsection 4.1 of this review
    • Germacranes readily undergo Cope rearrangement to elernanes, see subsection 4.1 of this review.
  • 53
    • 0001613158 scopus 로고
    • For a review of the titanium-induced dicarbonyl-coupling reactions, see: McMurry JE. Acc. Chem. Res. 1983;16:405-411.
    • (1983) Acc. Chem. Res. , vol.16 , pp. 405-411
    • McMurry, J.E.1
  • 64
    • 0028828639 scopus 로고
    • and references cited therein
    • The intramolecular cyclopropanation reaction of carbenoids derived from farnesol invariably produces the bicycloheptane ring system, see: Gant TG, Noe MC, Corey EJ. Tetrahedron Lett. 1995;36:8745-8748 and references cited therein.
    • (1995) Tetrahedron Lett. , vol.36 , pp. 8745-8748
    • Gant, T.G.1    Noe, M.C.2    Corey, E.J.3
  • 76
    • 84952239308 scopus 로고
    • For an extensive review of the Wharton reaction, see: Caine D. Org. Prep. Proced. Int. 1988;20:1-51.
    • (1988) Org. Prep. Proced. Int. , vol.20 , pp. 1-51
    • Caine, D.1
  • 104
    • 0013522859 scopus 로고
    • A similar methodology has also been used to construct -membered ring systems, see: Clark DA, Fuchs PL. J. Am. Chem. Soc. 1979;101:3567-3576.
    • (1979) J. Am. Chem. Soc. , vol.101 , pp. 3567-3576
    • Clark, D.A.1    Fuchs, P.L.2
  • 138
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    • See also references 95a, 95c and 95f
    • (c) See also references 95a, 95c and 95f.
    • J. Org. Chem.
  • 144
  • 145
    • 0000746177 scopus 로고
    • Trost BM, Fleming I, Paquette LA, editors. New York: Pergamon Press
    • For a comprehensive discussion of these effects, see: Hill RK. In: Trost BM, Fleming I, Paquette LA, editors. Comprehensive Organic Synthesis. Vol. 5. New York: Pergamon Press, 1991:785.
    • (1991) Comprehensive Organic Synthesis , vol.5 , pp. 785
    • Hill, R.K.1
  • 158
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    • Stuttgart: Georg Thieme Verlag
    • Frauenrath H. In: Houben-Weyl Vol. E 21 d. Stuttgart: Georg Thieme Verlag, 1995:3696-3726.
    • (1995) Houben-Weyl , vol.E21D , pp. 3696-3726
    • Frauenrath, H.1
  • 165
    • 0002202998 scopus 로고
    • N.Y.
    • For a review of the oxy-Cope rearrangement, see: Wilson SR. Org. React.(N.Y.) 1993;43:93-250.
    • (1993) Org. React. , vol.43 , pp. 93-250
    • Wilson, S.R.1


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.