(R)-de-O-Methyllasiodiplodin

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: (R)-de-O-Methyllasiodiplodin
• 英文别名: (3R)-de-O-methyllasiodiplodin；desmethyl lasiodiplodin；(R)-de-O-methyllasioplodin；(4R)-14,16-dihydroxy-4-methyl-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-2-one
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: NFEVFCAOVZCHBN-LLVKDONJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.56
• 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：

  丁酸酐 、 (R)-de-O-Methyllasiodiplodin 在 三乙胺 作用下， 以 二氯甲烷 为溶剂， 以80%的产率得到[(4R)-16-butanoyloxy-4-methyl-2-oxo-3-oxabicyclo[10.4.0]hexadeca-1(12),13,15-trien-14-yl] butanoate
  参考文献：
  名称：

  Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor

  摘要：

  Macrolide (R)-de-O-methyllasiodiplodin (1), discovered to be a potent nonsteroidal antagonist of the mineralocorticoid receptor (MR), was synthesized via an efficient method and evaluated for MR antagonistic activity together with its analogs. Among all the tested compounds, compounds 18a, 18b and 18c, exhibited more potent antagonistic activity against MR with IC50 values ranging from 0.58 to 1.11 mu M. Generally, it was obviously demonstrated that acetylation at phenolic hydroxyl groups and the ring size in analogs of 1 were very important for MR antagonist activity. (c) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.bmcl.2010.12.101
• 作为产物：
  描述：

  7-羟基庚酸甲酯 在 六甲基磷酰三胺 、 氢氧化钾 、 disodium hydrogenphosphate 、 sodium amalgam 、 2,2'-二硫二吡啶 、 silver perchlorate 、 三溴化硼 、 镍 、 二异丁基氢化铝 、 碳酸氢钠 、 三乙胺 、 三苯基膦 、 sodium iodide 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 乙醇 、 正己烷 、 二氯甲烷 、 乙二醇 、 丙酮 为溶剂， 反应 84.08h， 生成 (R)-de-O-Methyllasiodiplodin
  参考文献：
  名称：

  奥来酸类大环内酯类化合物的不对称合成：lasiodiplodin的例子

  摘要：

  描述了甲基拉西地夫定的两种对映异构体的不对称合成。手性中心是在合成的最后步骤中通过不对称诱导手性亚砜基而产生的。

  DOI：

  10.1016/0957-4166(90)90013-z

文献信息

• A Short and Efficient Approach for the Total Synthesis of (<i>S</i>)-Zearalenone and (<i>R</i>)-De-<i>O</i>-methyllasiodiplodin by Using Stille and RCM Protocols
  作者：Sujit Kumar Dey、Mohammad Ataur Rahman、Ahmad Alkhazim Alghamdi、Basi V. Subba Reddy、Jhillu S. Yadav

  DOI：10.1002/ejoc.201501545

  日期：2016.3

  A concise, flexible, and linear approach has been devised for the total synthesis of the resorcinylic acid lactones (S)-zearalenone (2) and (R)-de-O-methyllasiodiplodin (4) by using a Stille cross-coupling strategy. The other key steps of the synthesis include a ring-closing metathesis (RCM), a chemoselective reduction of an α,β-unsaturated ketone, and a transesterification reaction.

  通过使用 Stille 交叉偶联策略，设计了一种简洁、灵活和线性的方法来全合成间苯二酸内酯 (S)-玉米赤霉烯酮 (2) 和 (R)-de-O-methyllasiodiplodin (4)。合成的其他关键步骤包括闭环复分解 (RCM)、α,β-不饱和酮的化学选择性还原和酯交换反应。
• SOLLADIE, GUY;RUBIO, ALMUDENA;CARMEN, CARRENO M.;GARCIA, RUANO JOSE L., TETRAHEDRON: ASYMMETRY, 1,(1990) N, C. 187-198
  作者：SOLLADIE, GUY、RUBIO, ALMUDENA、CARMEN, CARRENO M.、GARCIA, RUANO JOSE L.

  DOI：——

  日期：——
• Synthesis, modification, and evaluation of (R)-de-O-methyllasiodiplodin and analogs as nonsteroidal antagonists of mineralocorticoid receptor
  作者：Cheng-Shi Jiang、Rong Zhou、Jing-Xu Gong、Li-Li Chen、Tibor Kurtán、Xu Shen、Yue-Wei Guo

  DOI：10.1016/j.bmcl.2010.12.101

  日期：2011.2

  Macrolide (R)-de-O-methyllasiodiplodin (1), discovered to be a potent nonsteroidal antagonist of the mineralocorticoid receptor (MR), was synthesized via an efficient method and evaluated for MR antagonistic activity together with its analogs. Among all the tested compounds, compounds 18a, 18b and 18c, exhibited more potent antagonistic activity against MR with IC50 values ranging from 0.58 to 1.11 mu M. Generally, it was obviously demonstrated that acetylation at phenolic hydroxyl groups and the ring size in analogs of 1 were very important for MR antagonist activity. (c) 2010 Elsevier Ltd. All rights reserved.
• Asymmetric synthesis of orsellinic acid type macrolides: The example of lasiodiplodin
  作者：Guy Solladié、Almudena Rubio、M.Carmen Carreño、JoséL. García Ruano

  DOI：10.1016/0957-4166(90)90013-z

  日期：1990.1

  The asymmetric synthesis of both enantiomers of methyl lasiodiplodin is described. The chiral centers were created in the very last steps of the synthesis by asymmetric induction of a chiral sulfoxide group.

  描述了甲基拉西地夫定的两种对映异构体的不对称合成。手性中心是在合成的最后步骤中通过不对称诱导手性亚砜基而产生的。