Substituted 1,7-dioxabicyclo[3.3.0]octanes: New easy access to the perhydrofurofuran core of aflatoxins and analogues

被引:42
作者
Alonso, F [1 ]
Lorenzo, E [1 ]
Yus, M [1 ]
机构
[1] UNIV ALICANTE,FAC CIENCIAS,DEPT QUIM ORGAN,E-03080 ALICANTE,SPAIN
关键词
D O I
10.1016/S0040-4039(97)00278-5
中图分类号
O62 [有机化学];
学科分类号
070303 ; 081704 ;
摘要
The reaction of 3-chloro-2-(chloromethyl)-1-propene(1) with lithium and a catalytic amount of naphthalene in the presence of different carbonyl compounds in THF a -78 degrees C affords, after hydrolysis, the corresponding methylenic diols 2, which by a tandem hydroboration-oxidation with hydrogen peroxide followed by treatment with PCC (for ketone derivatives) or RuCl2(PPh(3))(3) (for aldehyde derivatives) yields the expected perhydrofurofurans 3. (C) 1997 Elsevier Science Ltd.
引用
收藏
页码:2187 / 2190
页数:4
相关论文
共 31 条
  • [1] Arene-catalysed lithiation of triflates and triflamides under Barbier-type conditions: An indirect transformation of alcohols and amines into organolithium compounds
    Alonso, E
    Ramon, DJ
    Yus, M
    [J]. TETRAHEDRON, 1996, 52 (45) : 14341 - 14348
  • [2] Blomberg C., 1993, The Barbier reaction and related one-step processes
  • [3] BUCHI G, 1981, J AM CHEM SOC, V103, P3497, DOI 10.1021/ja00402a039
  • [4] BUCHI G, 1967, J AM CHEM SOC, V89, P6745, DOI 10.1021/ja01001a062
  • [5] Busby WF, 1984, ACS MONOGR SER, V182, P945
  • [6] SYNTHESES OF TETRAHYDROFURO[2,3-B]BENZOFURANS - A SYNTHESIS OF (H-AFLATOXIN-B2
    CASTELLINO, AJ
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1986, 51 (07) : 1006 - 1011
  • [7] Antibacterial neoclerodane diterpenoids from Ajuga lupulina
    Chen, H
    Tan, RX
    Liu, ZL
    Zhang, Y
    Yang, L
    [J]. JOURNAL OF NATURAL PRODUCTS, 1996, 59 (07): : 668 - 670
  • [8] SYNTHESIS OF THE ENANTIOMERIC FUROBENZOFURANS, LATE PRECURSORS FOR THE SYNTHESIS OF (+)-AFLATOXINS AND (-)-AFLATOXINS B-1, B-2, G(1), AND G(2)
    CIVITELLO, ER
    RAPOPORT, H
    [J]. JOURNAL OF ORGANIC CHEMISTRY, 1994, 59 (14) : 3775 - 3782
  • [9] COREY EJ, 1975, TETRAHEDRON LETT, P2647
  • [10] *COUNC AGR SCI TEC, 1988, MYC EC HLTH RISKS