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Volumn 63, Issue 25, 1998, Pages 9166-9176

Carbocationic rearrangements of silphinane derivatives

Author keywords

[No Author keywords available]

Indexed keywords

ALPHA TERRECYCLENE; ISOCOMENE; MESYLIC ACID; SESQUITERPENE; SILPHIN 1ALPHA MESYLATE; SILPHINANE; UNCLASSIFIED DRUG;

EID: 0032509255     PISSN: 00223263     EISSN: None     Source Type: Journal    
DOI: 10.1021/jo971579v     Document Type: Article
Times cited : (39)

References (72)
  • 6
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    • Chapman and Hall: London
    • (b) Bohlmann's biogenetically consistent numbering system for presilphiperfolanes, silphiperfolanes, and silphinanes seems to be generally accepted for these three sesquiterpene families: see Dictionary of Natural Products; Chapman and Hall: London, 1994; Vol. 7, p xxvii. In view of the biogenetic connections discussed in this paper, we recommend its logical extension to the isocomane and modhephane families also.
    • (1994) Dictionary of Natural Products , vol.7
  • 24
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    • For reviews on cyclopentanoid natural products, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152; 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1979) Top. Curr. Chem. , vol.79 , pp. 41-152
    • Paquette, L.A.1
  • 25
    • 20644435283 scopus 로고
    • For reviews on cyclopentanoid natural products, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152; 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1984) Top. Curr. Chem. , vol.119 , pp. 1-147
  • 26
    • 0004154187 scopus 로고
    • Springer-Verlag: Berlin
    • For reviews on cyclopentanoid natural products, see: (a) Paquette, L. A. Top. Curr. Chem. 1979, 79, 41-152; 1984, 119, 1-147. (b) Paquette, L. A.; Doherty, A. M. Polyquinane Chemistry; Springer-Verlag: Berlin, 1987.
    • (1987) Polyquinane Chemistry
    • Paquette, L.A.1    Doherty, A.M.2
  • 27
    • 0000558630 scopus 로고
    • For reviews and leading references on sesquiterpene biosynthesis, see: (a) Cane, D. E. Chem. Rev. 1990, 90, 1089-1103. (b) Cane, D. E. Acc. Chem. Res. 1985, 18, 220. (c) Cane, D. E. In Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds. Wiley: New York, 1981; Vol. 1, Chapter 6.
    • (1990) Chem. Rev. , vol.90 , pp. 1089-1103
    • Cane, D.E.1
  • 28
    • 0001312578 scopus 로고
    • For reviews and leading references on sesquiterpene biosynthesis, see: (a) Cane, D. E. Chem. Rev. 1990, 90, 1089-1103. (b) Cane, D. E. Acc. Chem. Res. 1985, 18, 220. (c) Cane, D. E. In Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds. Wiley: New York, 1981; Vol. 1, Chapter 6.
    • (1985) Acc. Chem. Res. , vol.18 , pp. 220
    • Cane, D.E.1
  • 29
    • 0000558630 scopus 로고
    • Porter, J. W., Spurgeon, S. L., Eds. Wiley: New York, Chapter 6
    • For reviews and leading references on sesquiterpene biosynthesis, see: (a) Cane, D. E. Chem. Rev. 1990, 90, 1089-1103. (b) Cane, D. E. Acc. Chem. Res. 1985, 18, 220. (c) Cane, D. E. In Biosynthesis of Isoprenoid Compounds; Porter, J. W., Spurgeon, S. L., Eds. Wiley: New York, 1981; Vol. 1, Chapter 6.
    • (1981) Biosynthesis of Isoprenoid Compounds , vol.1
    • Cane, D.E.1
  • 45
    • 20644462304 scopus 로고    scopus 로고
    • note
    • 19a
  • 54
    • 0003183816 scopus 로고
    • (±)-Isocomene was synthesized according to literature procedures: Pirrung, M. C. J. Am. Chem. Soc. 1981, 103, 82-87.
    • (1981) J. Am. Chem. Soc. , vol.103 , pp. 82-87
    • Pirrung, M.C.1
  • 55
    • 0027395867 scopus 로고
    • Curran, D. P.; Shen, W. Tetrahedron 1993, 49, 755. We are grateful to Professor Curran for providing a sample of (±)-modhephene for these comparisons.
    • (1993) Tetrahedron , vol.49 , pp. 755
    • Curran, D.P.1    Shen, W.2
  • 58
    • 20644462496 scopus 로고
    • Olah, G. A., Schleyer, P. von R., Eds.; Wiley: New York, Chapter 24
    • Sargent, G. D. In Carbonium Ions; Olah, G. A., Schleyer, P. von R., Eds.; Wiley: New York, 1972; Vol. 3, Chapter 24, p 1162.
    • (1972) Carbonium Ions , vol.3 , pp. 1162
    • Sargent, G.D.1
  • 60
    • 0001543521 scopus 로고
    • Olah, G. A., Schleyer, P. von R., Eds; Wiley: New York, Chapter 32
    • For reviews on bridgehead reactivity, see: (a) Fort, R. C., Jr. In Carbonium Ions; Olah, G. A., Schleyer, P. von R., Eds; Wiley: New York, 1972; Vol. 4, Chapter 32, 1783-1835. (b) Liebman, J. F.; Greenberg, A. Chem. Rev. 1976, 76, 311-365 and Table 5 of this reference, p 321.
    • (1972) Carbonium Ions , vol.4 , pp. 1783-1835
    • Fort Jr., R.C.1
  • 61
    • 0001590325 scopus 로고
    • Table 5 of this reference, p 321
    • For reviews on bridgehead reactivity, see: (a) Fort, R. C., Jr. In Carbonium Ions; Olah, G. A., Schleyer, P. von R., Eds; Wiley: New York, 1972; Vol. 4, Chapter 32, 1783-1835. (b) Liebman, J. F.; Greenberg, A. Chem. Rev. 1976, 76, 311-365 and Table 5 of this reference, p 321.
    • (1976) Chem. Rev. , vol.76 , pp. 311-365
    • Liebman, J.F.1    Greenberg, A.2


* 이 정보는 Elsevier사의 SCOPUS DB에서 KISTI가 분석하여 추출한 것입니다.