2-aryl-5-epoxynitrile anion cyclizations:: Total syntheses of (±)-α-cuparenone and (±)-epilaurene

被引:6
作者
Avila-Zárraga, JG
Maldonado, LA
机构
[1] Natl Autonomous Univ Mexico, Inst Quim, Mexico City 04510, DF, Mexico
[2] Natl Autonomous Univ Mexico, Div Estudios Posgrado, Mexico City 04510, DF, Mexico
关键词
D O I
10.1246/cl.2000.512
中图分类号
O6 [化学];
学科分类号
0703 ;
摘要
Total syntheses of the cyclopentane sesquiterpenes of the title using an epoxynitrile anion cyclization reaction as key step, are described. The preferential formation of the cyclopentane ring from a terminal disubstituted 5-epoxynitrile (e.g. 2b) had not previously been observed. The 2-aryl substituent is reasonably assumed to be responsible for this divergence.
引用
收藏
页码:512 / 513
页数:2
相关论文
共 13 条
  • [1] ACHINI R, 1975, TETRAHEDRON LETT, P369
  • [2] Arseniyadis S., 1984, ORG REACTIONS, V31, P1, DOI DOI 10.1002/0471264180.OR031.01
  • [3] 1-Phenyl-2t-(2-hydroxy-2-propyl)-1r-cyclobutanecarboxamide
    Avila, G
    Maldonado, LA
    Toscano, RA
    [J]. JOURNAL OF CHEMICAL CRYSTALLOGRAPHY, 1997, 27 (02) : 125 - 128
  • [4] BIERNACKI W, 1979, SYNTHESIS-STUTTGART, P37
  • [5] 2-methylcyclopentane-1,3-dione: An efficient synthon for the synthesis of (+/-)-alpha-cuparenone.
    Cossy, J
    Gille, B
    BouzBouz, S
    Bellosta, V
    [J]. TETRAHEDRON LETTERS, 1997, 38 (23) : 4069 - 4070
  • [6] ASYMMETRIC CONSTRUCTION OF QUATERNARY CARBONS FROM CHIRAL MALONATES - TOTAL SYNTHESES OF (+)-EPILAURENE AND (-)-ISOLAURENE
    FADEL, A
    CANET, JL
    SALAUN, J
    [J]. TETRAHEDRON-ASYMMETRY, 1993, 4 (01) : 27 - 30
  • [7] LAURENE A SESQUITERPENE HYDROCARBON FROM LAURENCIA SPECIES
    IRIE, T
    SUZUKI, T
    YASUNARI, Y
    KUROSAWA, E
    MASAMUNE, T
    [J]. TETRAHEDRON, 1969, 25 (02) : 459 - &
  • [8] A short and efficient total synthesis of (+/-)alpha-cuparenone
    Kulkarni, MG
    Pendharkar, DS
    [J]. TETRAHEDRON, 1997, 53 (09) : 3167 - 3172
  • [9] An efficient total synthesis of (+/-)-laurene
    Kulkarni, MG
    Pendharkar, DS
    [J]. JOURNAL OF THE CHEMICAL SOCIETY-PERKIN TRANSACTIONS 1, 1997, (21): : 3127 - 3128
  • [10] LALLEMAND JY, 1975, TETRAHEDRON LETT, P585