(-)-leubethanol | 1332615-10-7

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (-)-leubethanol
• 英文别名: Leubethanol；(5S,8R)-3,8-dimethyl-5-[(2S)-6-methylhept-5-en-2-yl]-5,6,7,8-tetrahydronaphthalen-1-ol
• CAS: 1332615-10-7
• 化学式: C₂₀H₃₀O
• 分子量: 286.458
• InChiKey: WQVJUBFKFCDYDQ-BBWFWOEESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  21
• 可旋转键数：
  4
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  20.2
• 氢给体数：
  1
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  (-)-leubethanol 在 palladium 10% on activated carbon 、 氢气 作用下， 以 乙醇 为溶剂， 以95%的产率得到C₂₀H₃₂O
  参考文献：
  名称：

  Diterpenes Synthesized from the Natural Serrulatane Leubethanol and Their in Vitro Activities against Mycobacterium tuberculosis

  摘要：

  合成了十七种天然二萜化合物蕾伯醇的新衍生物，包括一些潜在的前药，这些衍生物在脂肪链的功能性变化或芳香环和酚羟基的修饰方面进行了改造，并采用MABA技术在体外测试了它们对H37Rv株结核分枝杆菌的活性。一些化合物显示出比蕾伯醇更高的抗分枝杆菌选择性指数。

  DOI：

  10.3390/molecules20047245
• 作为产物：
  描述：

  2-(R)-(1S,4R,5-methoxy-7-methyl-1,2,3,4-tetrahydronaphthalen-1-yl)-propan-1-ol 在 正丁基锂 、 草酰氯 、 palladium on activated charcoal 、 氢气 、 二异丁基氢化铝 、 二甲基亚砜 、 乙硫醇钠 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 乙酸乙酯 、 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 199.5h， 生成 (-)-leubethanol
  参考文献：
  名称：

  Total synthesis and structural confirmation of the antibacterial diterpene leubethanol

  摘要：

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2013.05.082

文献信息

• Asymmetric Total Syntheses of Di‐ and Sesquiterpenoids by Catalytic C−C Activation of Cyclopentanones
  作者：Si‐Hua Hou、Adriana Y. Prichina、Mengxi Zhang、Guangbin Dong

  DOI：10.1002/anie.201915821

  日期：2020.5.11

  The key step in these syntheses involve a Rh-catalyzed C-C/C-H activation cascade of 3-arylcyclopentanones, which provides a rapid and enantioselective route to access the polysubstituted tetrahydronaphthalene cores presented in these natural products. Other important features include 1) the direct C-H amination of the tetralone substrate in the synthesis of (-)-microthecaline A, 2) the use of phosphoric

  为了展示催化 CC 活化对张力较小的底物的合成效用，这里描述了天然产物 (-)-microthecaline A、(-)-leubehanol、(+)-pseudopteroxodium、(+)- 的集体和简明合成。 seco-pseudopteroxilla、pseudopterosin AF 和 GJ 苷元以及 (+)-heritinin。这些合成的关键步骤涉及 Rh 催化的 3-芳基环戊酮的 CC/CH 活化级联，这提供了一种快速且对映选择性的途径来获取这些天然产物中存在的多取代四氢萘核心。其他重要特征包括 1) 在 (-)-微壳碱 A 合成中对四氢萘酮底物进行直接 CH 胺化，2) 使用磷酸来提高 CC 活化反应中有问题的环戊酮底物的效率和区域选择性，以及 3)通过烯丙基环脱氢偶联将沙鲁坦直接转化为两性双萜。
• Enantioselective Total Syntheses of Various Amphilectane and Serrulatane Diterpenoids via Cope Rearrangements
  作者：Xuerong Yu、Fan Su、Chang Liu、Haosen Yuan、Shan Zhao、Zhiyao Zhou、Tianfei Quan、Tuoping Luo

  DOI：10.1021/jacs.6b02624

  日期：2016.5.18

  was optimized to afford a precursor. The preparation of the chiral β-ketoester as a starting material was established via an optimized asymmetric 1,4-addition followed by trapping with Mander's reagent, and this initially installed stereogenic center provided good control in the subsequent introduction of all the other stereocenters. A rarely investigated one-pot conversion of α-pyrone into phenol was

  Ampilectane 和 serrulatane 天然产物是结构和立体化学上复杂的化合物，显示出从抗炎到抗结核的各种有效药理活性。已经开发了该系列天然产物的一般合成路线，该路线完成了许多amphilectane 和serrulatane 天然产物。关键步骤采用由金催化或热条件促进的立体选择性 Cope 重排，同时优化区域选择性金催化的 6-endo-dig 环化以提供前体。手性 β-酮酯作为起始材料的制备是通过优化的不对称 1,4-加成，然后用曼德试剂捕获，这个最初安装的立体中心在随后引入所有其他立体中心时提供了良好的控制。还研究了很少研究的 α-吡喃酮向苯酚的一锅法转化，以实现合成。DFT 计算解释了中间体 Cope 重排的高立体选择性，最终导致了 amphilectolide 和 caribenol A。
• Synthesis of Leubethanol derivatives and evaluation against Mycobacterium tuberculosis
  作者：Jonathan Perez-Meseguer、Esther del Olmo、Blanca Alanis-Garza、Ricardo Escarcena、Elvira Garza-González、Ricardo Salazar-Aranda、Arturo San Feliciano、Noemí Waksman de Torres

  DOI：10.1016/j.bmc.2012.04.059

  日期：2012.7

  Twenty-five derivatives of the natural diterpene leubethanol, including several potential pro-drugs, with changes in the functionality of the aliphatic chain or modifications of the phenolic group, were synthesized and tested in vitro by the MABA technique for their activity against the H37Rv strain of Mycobacterium tuberculosis. Several compounds showed antimycobacterial potencies similar to that of the lead compound and two of them displayed higher selectivity indexes. (C) 2012 Elsevier Ltd. All rights reserved.
• Diterpenes Synthesized from the Natural Serrulatane Leubethanol and Their in Vitro Activities against Mycobacterium tuberculosis
  作者：Ricardo Escarcena、Jonathan Perez-Meseguer、Esther del Olmo、Blanca Alanis-Garza、Elvira Garza-González、Ricardo Salazar-Aranda、Noemí Waksman de Torres

  DOI：10.3390/molecules20047245

  日期：——

  Seventeen new derivatives of the natural diterpene leubethanol, including some potential pro-drugs, with changes in the functionality of the aliphatic chain or modifications of aromatic ring and the phenolic group, were synthesized and tested in vitro by the MABA technique for their activity against the H37Rv strain of Mycobacterium tuberculosis. Some compounds showed antimycobacterial selectivity indices higher than leubethanol.

  合成了十七种天然二萜化合物蕾伯醇的新衍生物，包括一些潜在的前药，这些衍生物在脂肪链的功能性变化或芳香环和酚羟基的修饰方面进行了改造，并采用MABA技术在体外测试了它们对H37Rv株结核分枝杆菌的活性。一些化合物显示出比蕾伯醇更高的抗分枝杆菌选择性指数。
• Total synthesis and structural confirmation of the antibacterial diterpene leubethanol
  作者：Jessica M.H. Lu、Michael V. Perkins、Hans J. Griesser

  DOI：10.1016/j.tet.2013.05.082

  日期：2013.8

  We report the total synthesis of leubethanol (1), a serrulatane compound that has recently been reported as having considerable antibacterial activity against multidrug-resistant bacteria, such as Staphylococcus aureus, and is of interest for applications in the control of bacterial biofilms in human medicine. Our synthetic route begins with (-)-isopulegol (4) and key steps include substrate directed hydroboration to generate the C1' stereocentre and formation of the aromatic ring via the alpha-oxoketene-S,S-acetal intermediate 3. Overall the conversion of (-)-isopulegol (4) to leubethanol was achieved in 13 steps and an overall yield of 7%. Comparison of our spectroscopic data with those reported for leubethanol (1), isolated from Leucophyllum frutescens, verified the structure of the natural product. (C) 2013 Elsevier Ltd. All rights reserved.