goniobutenolide A

• 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: goniobutenolide A
• 英文别名: (5Z)-5-[(2S,3R)-2,3-dihydroxy-3-phenylpropylidene]furan-2-one
• 化学式: C₁₃H₁₂O₄
• 分子量: 232.236
• InChiKey: XDLSRIVPCBODNQ-RJSMLTLRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.7
• 重原子数：
  17
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.15
• 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：

  goniobutenolide A 在 偶氮二异丁腈 、 碘 、 三正丁基氢锡 、 碳酸氢钠 作用下， 以 甲苯 、 乙腈 为溶剂， 反应 145.0h， 生成 (4R)-(+)-crassalactone D
  参考文献：
  名称：

  Synthesis and antiproliferative activity of goniobutenolides A and B, 5-halogenated crassalactone D derivatives and the corresponding 7-epimers

  摘要：

  A new synthesis of goniobutenolides A (1) and B (2) and the corresponding 7-epimers has been achieved starting from diacetone D-glucose. The key step of the synthesis is a new one-pot sequence that commenced with Z-selective Wittig (or Horner-Wadsworth-Emmons) olefination, followed by successive gamma-lactonisation and beta-elimination. The above-mentioned unsaturated lactones were then converted to the corresponding 5-halogenated crassalactone D derivatives by using the appropriate haloetherification protocol. The most of synthesized compounds exhibited potent cytotoxic activities against a panel of tumour cell lines. The main structural features responsible for their antitumour potency have been revealed by means of SAR analysis. Flow cytometry data suggested that cytotoxic effects of these compounds in the culture of K562 cells might be mediated by apoptosis, additionally revealing that these molecules induced changes in cell cycle distribution of these cells. Results of semi-quantitative Western blot analysis indicate that the most of synthesized compounds induce apoptosis in a caspase-dependent manner. (C) 2015 Elsevier Masson SAS. All rights reserved.

  DOI：

  10.1016/j.ejmech.2015.12.011
• 作为产物：
  描述：

  D-扁桃酸 在 咪唑 、 盐酸 、 bis-triphenylphosphine-palladium(II) chloride 、 copper(l) iodide 、 二异丁基氢化铝 、 对甲苯磺酸 、 三乙胺 、 三苯基膦 作用下， 以 四氢呋喃 、 乙醚 、 N,N-二甲基甲酰胺 、 乙腈 为溶剂， 反应 82.5h， 生成 goniobutenolide A
  参考文献：
  名称：

  Efficient and diastereoselective synthesis of (+)-Goniobutenolide A via palladium-catalyzed ene-yne cross coupling-lactonization cascade

  摘要：

  (+)-Goniobutenolide A通过钯催化的烯炔交叉偶联-内酯化级联反应，从(R)-苯甘氨酸出发，在六个步骤中以21.4%的总产率合成。该反应对exo-环烯烃的几何结构控制近乎完全。版权 © 1996 Elsevier Science Ltd

  DOI：

  10.1016/s0040-4039(96)01972-7

文献信息

• Efficient and diastereoselective synthesis of (+)-Goniobutenolide A via palladium-catalyzed ene-yne cross coupling-lactonization cascade
  作者：Martin Kotora、Ei-ichi Negishi

  DOI：10.1016/s0040-4039(96)01972-7

  日期：1996.12

  (+)-Goniobutenolide A was synthesized in six steps in 21.4% overall yield from (R)-mandelic acid via Pd-catalyzed ene-yne cross coupling-lactonization cascade with essentially complete control of the exocyclic alkene geometry. Copyright (C) 1996 Elsevier Science Ltd

  (+)-Goniobutenolide A通过钯催化的烯炔交叉偶联-内酯化级联反应，从(R)-苯甘氨酸出发，在六个步骤中以21.4%的总产率合成。该反应对exo-环烯烃的几何结构控制近乎完全。版权 © 1996 Elsevier Science Ltd
• Stereoselective sulfoxide directed reduction of 1,2-diketo-derivatives to enantiomerically pure syn and anti 1,2-diols. Correction of the relative configuration by X-ray and chemical correlation to goniobutenolides A and B
  作者：Guy Solladié、Gilles Hanquet、Catherine Rolland

  DOI：10.1016/s0040-4039(98)80052-x

  日期：1999.1

  our recent report on the enantioselective synthesis of syn and anti 1,2-diols from oxalyl-di-(N-methyl-N-methoxyamide), an unfortunate sample inversion for 13C NMR analysis led us to an incorrect attribution of their relative configurations. We report now the correction of the configurations of these diols by X-ray analysis and chemical correlation to two known natural products, goniobutenolides A

  在我们最近的有关从草酰二-（N-甲基-N-甲氧基酰胺）对映异构体合成顺式和反式1,2-二醇的报告中，不幸的13 C NMR样品反演结果使我们误解了其相对分子质量配置。我们现在报告通过X射线分析和与两种已知的天然产物goniobutenolides A和B的化学相关性对这些二醇的构型进行校正。
• Synthetic studies towards naturally occurring γ-(<i>Z</i>)/(<i>E</i>)-alkylidenebutenolides through bimetallic cascade cyclization and an adventitious photoisomerization method
  作者：Shrestha Chatterjee、Ranjan Kumar Acharyya、Pratik Pal、Samik Nanda

  DOI：10.1039/d2ob00166g

  日期：——

  visible light-induced photoisomerization method of γ-(Z)-alkylidenebutenolides to their corresponding E-components was reported in this article. Initially, a series of naturally occurring enantiopure γ-(Z)-alkylidenebutenolides was synthesized by employing a “Pd–Cu” bimetallic cascade cyclization protocol. In the later part, the synthesized γ-(Z)-alkylidenebutenolides were photoisomerized in the presence

  本文报道了一种通用且灵活的可见光诱导γ-( Z )-亚烷基丁烯内酯光致异构化为其相应的E-组分的方法。最初，通过采用“Pd-Cu”双金属级联环化方案合成了一系列天然存在的对映体纯 γ-( Z )-亚烷基丁烯内酯。在后面的部分中，合成的 γ-( Z )-亚烷基丁烯内酯在三重光敏剂存在下以合理可接受的产率对 γ-( E )-亚烷基丁烯内酯进行光异构化。采用所开发的方法实现了 goniobutenolides、hygrophorones、ramariolide D、melodorinols/乙酰-melodorinols、versicolactones 和 phomopsolidones 的全合成。
• Studies on total syntheses of antitumor styryllactones: Stereoselective total syntheses of (+)-goniofufurone, (+)-goniobutenolide A, and (−)-goniobutenolide B
  作者：Chisato Mukai、Syuichi Hirai、In Jong Kim、Masaru Kido、Miyoji Hanaoka

  DOI：10.1016/0040-4020(96)00296-7

  日期：1996.5

  A highly stereoselective aldol reaction of the aldehyde 11, derived from (+)-tricarbonyl(η6-2-trimethylsilylbenzaldehyde)chromium(0) complex (4), with 2-trimethysilyloxyfuran afforded the γ-lactone derivative 13. The γ-lactone 13 was subsequently converted into three antitumor styryllactones, (+)-goniofufurone, (+)-goniobutenolide A, and (−)-goniobutenolide B.

  醛的高立体选择性醛醇缩合反应11，从（+）衍生的-三羰基（η 6 -2- trimethylsilylbenzaldehyde）铬（0）配合物（4），用2- trimethysilyloxyfuran得到γ内酯衍生物13。γ-内酯13随后被转化为三种抗肿瘤苯乙烯基内酯，（+）-goniofufurone，（+）-goniobutenolide A和（-）-goniobutenolideB。
• Divergent Synthesis of Cytotoxic Styryl Lactones Related to Goniobutenolides A and B, and to Crassalactone D
  作者：Velimir Popsavin、Ivana Kovačević、Goran Benedeković、Mirjana Popsavin、Vesna Kojić、Gordana Bogdanović

  DOI：10.1021/ol302860z

  日期：2012.12.7

  Goniobutenolides A (1) and B (2), crassalactone D (3), 4-epi-crassalactone D (4), and the corresponding 7-epimers have been synthesized starting from d-glucose. The key step in the synthesis of 1 and 2 is a new one-pot sequence comprised of a Z-selective Wittig olefination/lactonization/β-elimination. Preparation of 3 and 4 included the final 5-endo-trig spirocyclization of 1 and 2. The synthesized

  从d-葡萄糖开始合成了Goniobutenolides A（1）和B（2），crassalactone D（3），4- epi- crassalactone D（4）和相应的7表位受体。合成1和2的关键步骤是一个新的一锅法序列，该序列由Z选择性维蒂希烯化/内酯化/β-消除反应组成。3和4的制备包括1和2的最终5-内-trig螺环化。评价合成产物对所选肿瘤细胞系的体外抗增殖活性。