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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. shu

Stereoselective Synthesis of (±)-Epilitsenolide C₂ Using Mixed Higher Order Cyanocuprate

1.
Department of Chemistry, Hubei University, Wuhan 430062

Received Date: 28 August 1996
Available Online: 6 May 1997
Fund Project:

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.
- Epilitsenolide C₂,
- alkylidene-dihydro-hydroxy-methyl-furanone,
- mixed higher order cyanocuprate
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Stereoselective Synthesis of (±)-Epilitsenolide C2 Using Mixed Higher Order Cyanocuprate

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Stereoselective Synthesis of (±)-Epilitsenolide C₂ Using Mixed Higher Order Cyanocuprate