forbesione

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: forbesione
• 英文别名: (1R,2R,13R,15S)-6,8-dihydroxy-17,17-dimethyl-5,15-bis(3-methylbut-2-enyl)-3,16-dioxapentacyclo[11.4.1.02,11.02,15.04,9]octadeca-4,6,8,11-tetraene-10,14-dione
• 化学式: C₂₈H₃₂O₆
• 分子量: 464.558
• InChiKey: LWIGRTRTVVPXOZ-QLORKTMRSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  34
• 可旋转键数：
  4
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  93.1
• 氢给体数：
  2
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  forbesione 在 copper(l) iodide 、 potassium carbonate 、 potassium iodide 作用下， 以 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 5.5h， 生成 desoxymorellin
  参考文献：
  名称：

  Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

  摘要：

  The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.0(3,7)] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.029
• 作为产物：
  描述：

  在 盐酸 、 4-二甲氨基吡啶 、 copper(l) iodide 、 10 % Pd-BaSO4 、 palladium 10% on activated carbon 、 水 、 氢气 、 potassium carbonate 、 potassium iodide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 二氯甲烷 、 乙酸乙酯 、 丙酮 为溶剂， 反应 24.0h， 生成 forbesione
  参考文献：
  名称：

  Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A

  摘要：

  The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.0(3,7)] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2011.05.029

文献信息

• Synthesis and Anti-tumor Evaluation of B-ring Modified Caged Xanthone Analogues of Gambogic Acid
  作者：Xiang Li、Xiaojin Zhang、Xiaojian Wang、Nianguang Li、Changjun Lin、Yuan Gao、Zhuoqin Yu、Qinglong Guo、Qidong You

  DOI：10.1002/cjoc.201100045

  日期：2012.1

  products, has been reported to be a promising anti‐tumor agent. Previous studies have suggested that the planar B ring and the unique 4‐oxa‐tricyclo[4.3.1.03,7]dec‐2‐one caged motif were essential for anti‐tumor activity. To further explore the structure‐activity relationship (SAR) of caged Garcinia xanthones, two new series of B‐ring modified caged GA analogues 13a–13e and 15a–15e were synthesized utilizing

  藤黄（GA，1）是藤黄天然产物中最重要的成员，据报道是一种很有前途的抗肿瘤药物。先前的研究表明，平面B环和独特的4-oxa-tricyclo [4.3.1.0 3,7 ] dec-2-one笼状基序对于抗肿瘤活性至关重要。为了进一步探索笼状藤黄果的构效关系（SAR），利用克莱森/迪尔-阿尔德级联反应合成了两个新的B环修饰的笼状GA类似物13a – 13e和15a – 15e系列。随后，对这些化合物进行了体外评估通过MTT分析对A549，MCF-7，SMMC-7721和BGC-823癌细胞系的抗肿瘤活性 其中13b - 13e对几种癌细胞系表现出微摩尔抑制作用，与​​GA相比，其效力低约2-4倍。SAR分析显示，外围的二甲基基团对于维持抗肿瘤活性至关重要，并且B环C1位置的取代基对效能有重大影响，而C-2，C-3和C-4位置的修饰是相对可以容忍的。这些发现将加深我们对藤黄果SAR的了解，并导
• Microwave-Assisted Claisen Rearrangement/Diels–Alder Cascade reaction for the Synthesis of Caged <i>Garcinia</i> Natural Products and Analogues
  作者：Xiang Li、Xiaojin Zhang、Zhuoqin Yu、Xiaorong Liu、Qidong You、Qinglong Guo

  DOI：10.3184/174751911x13191290708355

  日期：2011.11

  and six known caged analogues were obtained. Compared with the traditional thermal method, the reaction time was reduced dramatically and the yield was greatly improved under microwave irradiation. In addition, the regioselectivity observed in the cascade reaction has also been rationalised. Garcinia have long been used in folk medicines for their healing, antibacterial, and cytotoxic activities.

  微波辅助 Claisen 重排/Diels-Alder 级联反应用于合成笼状藤黄天然产物和类似物，其中含有独特的 4-oxa-tricyclo[4.3.1.03,7]decan-2-one 支架，来自呫吨酮和色酮-基于基材。获得了福布松和丁酮以及两个新的和六个已知的笼状类似物。与传统的热法相比，在微波照射下反应时间大大缩短，收率大大提高。此外，在级联反应中观察到的区域选择性也得到了合理化。长期以来，藤黄因其愈合、抗菌和细胞毒性活性而被用于民间药物。
• Total synthesis of aldehyde-containing Garcinia natural products isomorellin and gaudichaudione A
  作者：Zong-Liang Liu、Xiao-Jian Wang、Nian-Guang Li、Hao-Peng Sun、Jin-Xin Wang、Qi-Dong You

  DOI：10.1016/j.tet.2011.05.029

  日期：2011.7

  The natural products, isomorellin and gaudichaudione A, with a 4-oxa-tricyclo[4.3.1.0(3,7)] dec-8-en-2-one scaffold were synthesized for the first time using an efficient method. The key improvement of this method was the simultaneous bisalkylation of 5,6-dihydroxyxanthone with the bulky 2-methylbutyne group. This method obviously shortened the synthetic route and enhanced the total yield. Four analogues named forbesione, desoxymorellin, desoxygaudichaudione A, and gambogin containing the same caged structure were prepared using this method. (C) 2011 Elsevier Ltd. All rights reserved.