The unexpected course of the reaction of steroid sapogenins with diacetoxyiodobenzene and BF3•Et2O in formic acid

被引：31
|
作者：
Iglesias-Arteaga, Martin A. [1 ]
Arcos-Ramos, Rafael O. [1 ]
Mendez-Stivalet, Jose M. [1 ]
机构：
[1] Univ Nacl Autonoma Mexico, Fac Quim, Dept Quim Organ, Mexico City 04510, DF, Mexico
来源：
TETRAHEDRON LETTERS | 2007年 / 48卷 / 42期
关键词：
D O I：
10.1016/j.tetlet.2007.08.071
中图分类号：
O62 [有机化学];
学科分类号：
070303 ; 081704 ;
摘要：
The reaction of steroid sapogenins of both the 25R and 25S series with diacetoxyiodobenzene and BF3 center dot Et2O in formic acid produced a mixture of an equatorial 23-formyloxysapogenin, a 16 beta,23:23,26-diepoxy-22-one and a bisnorcholanic lactone. The outcome of this reaction, that drastically differs from the same reaction in acetic acid, opens up new possibilities for the transformation of the side chain of steroid sapogenins. (C) 2007 Elsevier Ltd. All rights reserved.
引用
收藏
页码：7485 / 7488
页数：4
相关论文
共 50 条
  • [21] Epoxy resin - cyclic carbonate oligomer compositions cured with BF3·Et2O
    Polym Polym Compos, 1 (45-51):
  • [22] Unusual rearrangement of (cyclopropylmethoxy)benzene and its derivatives in the presence of BF3·Et2O
    D. O. Ptashko
    M. D. Khanova
    V. A. Dokichev
    Yu. V. Tomilov
    Russian Journal of Organic Chemistry, 2011, 47 : 1498 - 1500
  • [23] Studies on the BF3 · Et2O/MCM-41 solid acid catalyst and its catalytic performance
    Zhou, R.-X.
    Mo, L.-Y.
    Zhao, S.-F.
    Wang, Y.-J.
    Zheng, X.-M.
    2001, Higher Education Press (22):
  • [24] Role of temperature in [3+2]-cycloaddition of isoselenocyanates with oxiranes using BF3•Et2O
    Sengoden, Mani
    Punniyamurthy, Tharmalingam
    RSC ADVANCES, 2012, 2 (07): : 2736 - 2738
  • [25] Studies on the BF3 • Et2O/MCM-41 solid acid catalyst and its catalytic performance
    Zhou, RX
    Mo, LY
    Zhao, SF
    Wang, YJ
    Zheng, XM
    CHEMICAL JOURNAL OF CHINESE UNIVERSITIES-CHINESE, 2001, 22 (09): : 1576 - 1577
  • [26] BF3•Et2O promoted conjugate addition of ethanethiol to electron-deficient alkynes
    Zhou, Qing Fa
    Chu, Xue Ping
    Zhao, Shen
    Lu, Tao
    Tang, Wei Fang
    CHINESE CHEMICAL LETTERS, 2012, 23 (06) : 639 - 642
  • [27] An expedient and highly selective iodination of alcohols using a KI/BF3•Et2O system
    Bandgar, BP
    Sadavarte, VS
    Uppalla, LS
    TETRAHEDRON LETTERS, 2001, 42 (05) : 951 - 953
  • [28] Regioselective reduction of 4,6-O-benzylidenes using triethylsilane and BF3•Et2O
    Debenham, SD
    Toone, EJ
    TETRAHEDRON-ASYMMETRY, 2000, 11 (02) : 385 - 387
  • [29] Synthesis of substituted pyrrolidines by reaction of aryl-substituted vinylidenecyclopropanes with aromatic imines catalyzed by BF3•Et2O
    Stepakov, A. V.
    Larina, A. G.
    Radina, O. V.
    Boitsov, V. M.
    Molchanov, A. P.
    CHEMISTRY OF HETEROCYCLIC COMPOUNDS, 2008, 44 (04) : 430 - 434
  • [30] Synthesis of substituted pyrrolidines by reaction of aryl-substituted vinylidenecyclopropanes with aromatic imines catalyzed by BF3·Et2O
    A. V. Stepakov
    A. G. Larina
    O. V. Radina
    V. M. Boitsov
    A. P. Molchanov
    Chemistry of Heterocyclic Compounds, 2008, 44 : 430 - 434
12345