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Volumn 55, Issue 2, 2000, Pages 141-168

The role of germacrene D as a precursor in sesquiterpene biosynthesis: Investigations of acid catalyzed, photochemically and thermally induced rearrangements

Author keywords

Carbocations; Germacrene D; Isogermacrene D; Photochemistry; Rearrangement; Sesquiterpenes; Solidago spec.; Thermochemistry

Indexed keywords

ACID; AXANE DERIVATIVE; BOURBONANE DERIVATIVE; CADINANE DERIVATIVE; EUDESMANE DERIVATIVE; GERMACRENE D; ISODAUCANE DERIVATIVE; OPPOSITANE DERIVATIVE; SESQUITERPENE; SESQUITERPENE DERIVATIVE; UNCLASSIFIED DRUG;

EID: 0034641642     PISSN: 00319422     EISSN: None     Source Type: Journal    
DOI: 10.1016/S0031-9422(00)00266-1     Document Type: Article
Times cited : (228)

References (120)
  • 5
    • 0007620341 scopus 로고
    • Studies in sesquiterpene biogenesis: Implications of absolute configuration, new structure types, and efficient chemical simulation of pathways
    • Van Temelen, E.E. (Ed.), Bioorganic Chemistry, Vol. 2. Academic Press, New York
    • (1978) , pp. 1-37
    • Andersen, N.H.1    Ohto, Y.2    Syrdal, D.D.3
  • 7
    • 0028072115 scopus 로고
    • Synthetic studies of sesquiterpenes with a cis-fused decalin system, 4. Synthesis of (+)-5βH-eudesma-3,11-diene, (-)-5βH-eudesma-4α,11-diol, and (+)-5βH-eudesma-4α,11-diol, and structure revision of a natural cudcsmane-4,11-diol isolated from Pluchea arguta
    • (1994) J. Nat. Prod. , vol.57 , pp. 1189-1199
    • Ando, M.1    Arai, K.2    Kikuchi, K.3    Isogal, K.4
  • 8
    • 0027977929 scopus 로고
    • Synthetic studies of sesquiterpenes with a cis-fused decalin system, 5. A synthetic approach to the study of structure-activity relationships of the termiticidal norsesquiterpenoids, chamaecynone and related compounds
    • (1994) J. Nat. Prod. , vol.57 , pp. 924-933
    • Ando, M.1    Kikuchi, K.2    Isogal, K.3
  • 15
    • 0000026162 scopus 로고
    • The photolysis of some 1,6-dienes. Total synthesis of (±)-α-bourbonene
    • (1968) J. Org. Chem. , vol.33 , pp. 162-166
    • Brown, M.1
  • 16
    • 0007708349 scopus 로고    scopus 로고
    • Franz C., Mathe, A., Buchbauer, G. (Eds.), Essential Oils: Basic and Applied Research. Proceedings of the 27th International Symposium on Essential Oils, Vienna, Allured, Carol Stream, IL
    • (1996)
    • Bulow, N.1    Konig, W.A.2
  • 18
    • 0029050650 scopus 로고
    • Epicubenol synthase and the stereo-chemistry of the enzymatic cyclization of farnesyl and nerolidyl diphosphate
    • (1995) J. Am. Chem. Soc. , vol.117 , pp. 5602-5603
    • Cane, D.E.1    Tandon, M.2
  • 19
    • 0001312578 scopus 로고
    • Isoprenoid biosynthesis. Stereochemistry of the cyclization of allylic pyrophosphates
    • (1985) Acc. Chem. Res. , vol.18 , pp. 220-226
    • Cane, D.E.1
  • 22
    • 0007626727 scopus 로고
    • 152807y; Jpn. Kokai 77, 153,953
    • (1978) Chem. Abstr. , vol.88
  • 23
    • 0007620689 scopus 로고
    • 43415t; Jpn. Kokai Tokkyo Koho 81, 18,926
    • (1981) Chem. Abstr. , vol.95
  • 39
    • 5244247612 scopus 로고
    • Consistent force field calculations. III. Vibrationsm, conformations, and heats of hydrogenation of non-conjugated olefins
    • (1973) J. Am. Chem. Soc. , vol.95 , pp. 4121-4132
    • Ermer, O.1    Lifson, S.2
  • 43
    • 0007627240 scopus 로고
    • Dilithiated vicinal diester route to sesquiterpenes. Total synthesis of (±)-vetiselinene and the formal synthesis of other eudesmane sesquiterpenes
    • (1986) J. Org. Chem. , vol.51 , pp. 5450-5452
    • Garratt, P.J.1    Porter, J.R.2
  • 57
    • 0007627241 scopus 로고
    • Horwood, E. (Ed.), Organic photochemistry: A comprehensive treatment. PTR Prentice Hall, New York
    • (1992)
    • Horspool, W.1    Arnesto, D.2
  • 68
    • 0000799538 scopus 로고
    • Synthesis of terpenes containing the bicyclo[3.1.1]heptane ring system by the intramolecular [2+2]cycloaddition reaction of vinylketenes with alkenes. Preparation of chrysanthenone, β-pinene, β-cis-bergamotene, β-trans-bergamotene, β-copaene, and β-ylangene and lemnalol
    • (1987) J. Org. Chem. , vol.52 , pp. 1568-1576
    • Kulkarni, Y.S.1    Niwa, M.2    Ron, E.3    Snider, B.B.4
  • 71
    • 0000706265 scopus 로고
    • Terpenes and related systems. 16. Fate of representative bicyclic sesquiterpenes in strong acid medium. A general rearrangement of hydroazulene sesquiterpenes to decalin types
    • (1977) J. Org. Chem. , vol.42 , pp. 632-638
    • Mehta, G.1    Singh, B.2
  • 94
    • 0001503266 scopus 로고
    • Intramolekulare Wasserstoffverschiebung
    • (1966) Chimia , vol.20 , pp. 229-264
    • Roth, W.R.1
  • 105
    • 85008135336 scopus 로고
    • Stereoselective reactions. XVI. Total synthesis of (-)-β-bourbonene by emphoying asymmetric (2+2) photocycloaddition reaction of chiral butenolide
    • (1989) Chem. Pharm. Bull. , vol.37 , pp. 1201-1207
    • Tomioka, K.1    Tanaka, M.2    Koga, K.3


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.