ribisin A | 1415408-05-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并呋喃
• 英文名称: ribisin A
• 英文别名: Ribisin A；(2S,3R,4R)-3,4-dihydroxy-2-methoxy-3,4-dihydro-2H-dibenzofuran-1-one
• CAS: 1415408-05-7
• 化学式: C₁₃H₁₂O₅
• 分子量: 248.235
• InChiKey: AJGBUIPZHMUZEY-NQBHXWOUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.4
• 重原子数：
  18
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.31
• 拓扑面积：
  79.9
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  ribisin A 、 4-溴苯甲酰氯 在 吡啶 、 4-二甲氨基吡啶 作用下， 反应 3.0h， 以2.7 mg的产率得到[(2S,3R,4R)-4-(4-bromobenzoyl)oxy-2-methoxy-1-oxo-3,4-dihydro-2H-dibenzofuran-3-yl] 4-bromobenzoate
  参考文献：
  名称：

  Nerve Growth Factor-Potentiating Benzofuran Derivatives from the Medicinal FungusPhellinus ribis

  摘要：

  Four new benzofuran derivatives, ribisin A (1), ribisin B (2), ribisin C (3), and ribisin D (4), were isolated from the MeOH extract of the fruiting bodies of Phellinus ribis. Their structures including their absolute configurations were determined by NMR and CD exciton chirality methods. Compounds 1-4 were found to promote neurite outgrowth in NGF-mediated PC12 cells at concentrations ranging from 1 to 30 mu M. The structure-activity relationships of these compounds are also discussed.

  DOI：

  10.1021/np300566y
• 作为产物：
  描述：

  (((2R,4αR,6S,7R,8S,8αR)-6-methoxy-2-phenylhexahydropyrano[3,2-d][1,3]dioxine-7,8-diyl)bis(oxy))bis(tert-butyldimethylsilane) 在 咪唑 、 disodium hydrogenphosphate 、 双(三环己基膦)二氯化钯 、 palladium hydroxide, 20 wt% on carbon 、 mercury(II) diacetate 、 四丁基氟化铵 、 氢气 、 碘 、 氧气 、 sodium carbonate 、 甲基磺酰氯 、 三乙胺 、 三苯基膦 、 copper(l) chloride 、 palladium dichloride 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 吡啶 、 甲醇 、 四氯化碳 、 二氯甲烷 、 水 、 丙酮 为溶剂， -30.0~65.0 ℃ 、101.33 kPa 条件下， 反应 39.75h， 生成 ribisin A
  参考文献：
  名称：

  核糖素A的全合成

  摘要：

  从市售的甲基α-d-吡喃葡萄糖苷以11个步骤完成了天然产物核糖蛋白A的首次全合成，总收率为21.6％。通过Ferrier碳环化，Johnson碘化，Suzuki交叉偶联和Wacker氧化环化的关键反应，利用d-葡萄糖固有的手性构造了这种天然产物的高度氧化的苯并呋喃骨架。

  DOI：

  10.1016/j.tetlet.2013.12.052

文献信息

• Chemoenzymatic Synthesis of (−)-Ribisins A and B from Dibenzo[<i>b,d</i>]furan
  作者：Derek R. Boyd、Narain D. Sharma、Christopher J. McGivern、Paul J. Stevenson、Patrick Hoering、Christopher C. R. Allen

  DOI：10.1021/acs.joc.9b02171

  日期：2019.12.6

  monocyclic aromatic compounds, are valuable chiral pool intermediates for the synthesis of cyclic natural products. A drawback of this approach, to the synthesis of polycyclic secondary metabolites, is that additional rings must be annulated. To date, relatively few chiral natural products have been synthesized from polycyclic arene cis-dihydrodiols. Fungal metabolites, (-)-ribisins A and B, have now been

  衍生自单环芳族化合物的顺式-二氢二醇是用于合成环状天然产物的有价值的手性库中间体。这种方法对合成多环次级代谢产物的缺点是必须环化额外的环。迄今为止，由多环芳基顺式-二氢二醇合成了相对较少的手性天然产物。真菌代谢物（-）-核糖素A和B现在通过三环芳烃代谢物的官能团处理而获得，三环芳烃代谢物由甲苯二加氧酶催化的二苯并[b，d]呋喃的区域选择性和立体选择性顺式-二羟基化反应制得。合成序列比使用单环芳基顺式-二氢二醇的替代路线略短，并且不需要形成碳-碳键的反应。
• Chemoenzymatic Total Syntheses of Ribisins A, B, and D, Polyoxygenated Benzofuran Derivatives Displaying NGF-Potentiating Properties
  作者：Ping Lan、Martin G. Banwell、Anthony C. Willis

  DOI：10.1021/jo500210k

  日期：2014.4.4

  Total syntheses of the structures, 1, 2, and 4, assigned to the biologically active natural products ribisins A, B, and D, respectively, have been achieved using the microbially derived and enantiomerically pure cis-1,2-dihydrocatechol 5 as starting material. Key steps include Suzuki-Miyaura cross-coupling, intramolecular Mitsunobu, and tandem epoxidation/rearrangement reactions. As a result of these studies, the structures of ribisins A and D have been confirmed while that of congener B was shown to be represented by 31 rather than 2.
• Total synthesis of ribisin A
  作者：Chaoli Zhang、Jun Liu、Yuguo Du

  DOI：10.1016/j.tetlet.2013.12.052

  日期：2014.1

  The first total synthesis of natural product ribisin A has been achieved in 11 steps from commercially available methyl α-d-glucopyranoside with 21.6% overall yield. The highly oxygenated benzofuran skeleton of this natural product was constructed, taking advantages of the inherent chirality of d-glucose, through the key reactions of Ferrier carbocyclization, Johnson iodination, Suzuki cross-coupling

  从市售的甲基α-d-吡喃葡萄糖苷以11个步骤完成了天然产物核糖蛋白A的首次全合成，总收率为21.6％。通过Ferrier碳环化，Johnson碘化，Suzuki交叉偶联和Wacker氧化环化的关键反应，利用d-葡萄糖固有的手性构造了这种天然产物的高度氧化的苯并呋喃骨架。
• Nerve Growth Factor-Potentiating Benzofuran Derivatives from the Medicinal Fungus<i>Phellinus ribis</i>
  作者：Yuhong Liu、Miwa Kubo、Yoshiyasu Fukuyama

  DOI：10.1021/np300566y

  日期：2012.12.28

  Four new benzofuran derivatives, ribisin A (1), ribisin B (2), ribisin C (3), and ribisin D (4), were isolated from the MeOH extract of the fruiting bodies of Phellinus ribis. Their structures including their absolute configurations were determined by NMR and CD exciton chirality methods. Compounds 1-4 were found to promote neurite outgrowth in NGF-mediated PC12 cells at concentrations ranging from 1 to 30 mu M. The structure-activity relationships of these compounds are also discussed.