lissoclinolide

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 二氢呋喃
• 英文名称: lissoclinolide
• 英文别名: (5Z)-5-[(E)-4-hydroxybut-2-enylidene]-3-[(E)-3-hydroxyprop-1-enyl]furan-2-one
• 化学式: C₁₁H₁₂O₄
• 分子量: 208.214
• InChiKey: ZYNGLDJNLYFSIV-CZFMBXACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.2
• 重原子数：
  15
• 可旋转键数：
  4
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.18
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  lissoclinolide 、 乙酸酐 生成 [(E,4Z)-4-[4-[(E)-3-acetyloxyprop-1-enyl]-5-oxofuran-2-ylidene]but-2-enyl] acetate
  参考文献：
  名称：

  DAVIDSON, BRADLEY S.;IRELAND, CHRIS M., J. NATUR. PROD., 53,(1990) N, C. 1036-1038

  摘要：

  DOI：
• 作为产物：
  描述：

  (E,E)-2,4-己二烯二酸二甲酯 在 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 伯吉斯试剂 、 18-冠醚-6 、 三苯胂 、 potassium tert-butylate 、 水 、 三氧化硫吡啶 、 sodium hydride 、 二异丁基氢化铝 、 碳酸氢钠 、 氟化氢吡啶 、 溶剂黄146 、 二甲基亚砜 、 三乙胺 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 二氯甲烷 、 苯 为溶剂， 反应 48.08h， 生成 lissoclinolide
  参考文献：
  名称：

  Total Synthesis of Lissoclinolide by Acid-Induced Lactonization of an (E)-α-Bromo-γ,δ-Epoxy Acrylate Derivative

  摘要：

  The stereoselective total synthesis of lissoclinolide, a naturally occurring antibiotic and cytotoxic butenolide, was achieved in 10 steps including a highly E-selective Still-Gennari-type olefination and an acid-induced lactonization of an (E)-alpha-bromo-gamma,delta-epoxy acrylate derivative. The key regioselective 5-exo lactonization could be regulated by using AcOH under kinetically controlled conditions.

  DOI：

  10.3987/com-18-s(t)84

文献信息

• Stereocontrolled synthesis of lissoclinolide by sequential transition metal-catalyzed lactonization/cross-coupling reactions
  作者：Renzo Rossi、Fabio Bellina、Matteo Biagetti、Luisa Mannina

  DOI：10.1016/s0040-4039(98)01705-5

  日期：1998.10

  Lissoclinolide, 1, which is an antibiotic butenolide isolated from a Tuncate, has been synthesized stereoselectively by a reaction sequence in which the Ag(I)-catalyzed lactonization of (2E,6E)-2-bromo-8-hydroxy-2,6-octadien-4-ynoic acid, (E,E)-13, and the Pd/Cu-catalyzed cross-coupling reaction of so obtained (Z)-2-bromo-5-[(E)-4-hydroxy-2-butenylidene]-5H-furan-2-one, (Z,E)-14, with (E)-3-hydroxy-1-propenyltributylstannane

  Lissoclinolide 1是一种从Tuncate分离出来的抗生素丁烯内酯，它是通过反应序列立体选择性地合成的，在该反应序列中，Ag（I）催化了（2 E，6 E）-2-溴8-羟基-2的内酯化反应，6-辛二烯-4-壬酸（（E，E）-13以及由此获得的（Z）-2-溴-5-[[ E）-4-羟基]的Pd / Cu催化的交叉偶联反应（-2-丁烯叉基）-5 H-呋喃-2-酮（Z，E）-14和（E）-3-羟基-1-丙烯基三丁基锡烷15被用作关键步骤。
• Goerth, Felix C.; Brueckner, Reinhard, Synthesis, 1999, # S1, p. 1520 - 1528
  作者：Goerth, Felix C.、Brueckner, Reinhard

  DOI：——

  日期：——
• A highly efficient and selective synthesis of lissoclinolide featuring hydrogen transfer hydrozirconation,trans-selective Pd-catalyzed cross coupling of alkenylzirconiums with 1,1-dibromoalkenes and Ag-catalyzed lactonization providing(Z)-γ-alkylidenebutenolides
  作者：Caiding Xu、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(98)02394-6

  日期：1999.1

  An antibiotic lissoclinolide has been synthesized from propargyl alcohol in 9 steps and in 32% overall yield via (i) hydrogen transfer hydrozirconation of TBS-protected propargyl alcohol with i-BuZrCp2Cl, (ii) Pd-catalyzed trans-selective cross coupling of the hydrozirconation product with a key 1,1-dibromoalkene intermediate 5 and (iii) Ag-catalyzed lactonization of a trienynoic acid precursor 2. (C) 1998 Elsevier Science Ltd. All rights reserved.
• DAVIDSON, BRADLEY S.;IRELAND, CHRIS M., J. NATUR. PROD., 53,(1990) N, C. 1036-1038
  作者：DAVIDSON, BRADLEY S.、IRELAND, CHRIS M.

  DOI：——

  日期：——
• Total Synthesis of Lissoclinolide by Acid-Induced Lactonization of an (E)-α-Bromo-γ,δ-Epoxy Acrylate Derivative
  作者：Hiroshi Kogen、Kenichi Kobayashi、Keisuke Kuwahara、Kosaku Tanaka III、Risako Kunimura

  DOI：10.3987/com-18-s(t)84

  日期：——

  The stereoselective total synthesis of lissoclinolide, a naturally occurring antibiotic and cytotoxic butenolide, was achieved in 10 steps including a highly E-selective Still-Gennari-type olefination and an acid-induced lactonization of an (E)-alpha-bromo-gamma,delta-epoxy acrylate derivative. The key regioselective 5-exo lactonization could be regulated by using AcOH under kinetically controlled conditions.