引用本文:
陈祖兴, 李焰, 黄精美, 黄锦霞, 徐章煌. 混合高序铜法立体选择性合成(±)-Epilitsenolide C2[J]. 应用化学,
1997, 14(4): 111-113.
Citation: Chen Zuxing, Li Yan, Huang Jingmei, Huang Jinxia, Xu Zhanghuang. Stereoselective Synthesis of (±)-Epilitsenolide C2 Using Mixed Higher Order Cyanocuprate[J]. Chinese Journal of Applied Chemistry, 1997, 14(4): 111-113.
Citation: Chen Zuxing, Li Yan, Huang Jingmei, Huang Jinxia, Xu Zhanghuang. Stereoselective Synthesis of (±)-Epilitsenolide C2 Using Mixed Higher Order Cyanocuprate[J]. Chinese Journal of Applied Chemistry, 1997, 14(4): 111-113.
混合高序铜法立体选择性合成(±)-Epilitsenolide C2
摘要:
(3Z,4T,5T)-二氢-4-羟基-5-甲基-3-十四烷叉基-2(3H)-呋喃酮(简称Epilitsenolide C2(1)),属T-烷叉基-V-丁内酯类化合物,该类化合物多具有高细胞毒性和抗肿瘤活性.
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关键词:
- 烷叉基二氢羟基甲基(3H)呋喃酮
- / 混合高序铜
- / 立体选择性反应
English
Stereoselective Synthesis of (±)-Epilitsenolide C2 Using Mixed Higher Order Cyanocuprate
Abstract:
Lithium (T-caralkoxyvinyl) (2-thienyl) mixed higher order cyanocuprate(3), prepared by addition reaction of ethyl propiolate with (n-C13H27) (2-thienyl) CuCNLi2(2), was coupled with cis-bromopropylene under Pd(PPh3)4, gaving ethyl 1-(Z-propylidene)-1E-hexadecenate(4). The title compound (±)-epilitsenolide C2, (3Z,4T,5T)-4-hydroxyl-5-methyl-3-tetradecylidene-tetrahydro-2-furanone(1) was then selectively synthesized through epoxidation of the diene ester with m-chloroperbenzoic acid as oxidant and stereospecific lactonation by acid catalysis. The title compound(1) showed E:Z > 98:2 and cis:trans > 96:4. The method proposed has advantages of short route and high yield. Thus a new efficient method is presented for stereo selective synthesis of 3-alkylidene-4,5-dihydro-4-hydroxy-5-methyl-2(3H)-furanones.
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