emindole PB

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: emindole PB
• 英文别名: 2-[(3S,4aS,8S,10aR,10bS)-7,7,10b-trimethyl-8-[[1-(2-methylbut-3-en-2-yl)indol-3-yl]methyl]-2,3,4a,5,8,9,10,10a-octahydro-1H-benzo[f]chromen-3-yl]propan-2-ol
• 化学式: C₃₃H₄₇NO₂
• 分子量: 489.742
• InChiKey: BDIIYBDSOVLLMV-CWHSOGNVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.4
• 重原子数：
  36
• 可旋转键数：
  5
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  34.4
• 氢给体数：
  1
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  (1-甲苯磺酰-1H-吲哚-3-基)甲醇 在 三乙基硅烷 、 aluminum (III) chloride 、 sodium tetrahydroborate 、 氯化亚砜 、 三甲基铝 、 copper diacetate 、 palladium diacetate 、 silver trifluoroacetate 、 二异丙胺 、 potassium hydroxide 、 lithium hexamethyldisilazane 作用下， 以 四氢呋喃 、 甲醇 、 乙醚 、 乙醇 、 正己烷 、 二氯甲烷 、 1,2-二氯乙烷 、 乙腈 为溶剂， 反应 97.2h， 生成 emindole PB
  参考文献：
  名称：

  Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy

  摘要：

  We report the total syntheses of two indole diterpenoid natural products, paspaline A and emindole PB. Paspaline A is synthesized in a 9-step sequence from commercially available materials. The first total synthesis of emindole PB is accomplished in 13 steps and confirms a previously ambiguous structural assignment. Density functional theory calculations are utilized to interrogate the key carbocationic rearrangement in a predictive capacity to aid in the selection of the most favorable precursor substrate. This work highlights how retro-synthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.

  DOI：

  10.1021/jacs.8b13127

文献信息

• Total Synthesis of Paspaline A and Emindole PB Enabled by Computational Augmentation of a Transform-Guided Retrosynthetic Strategy
  作者：Daria E. Kim、Joshua E. Zweig、Timothy R. Newhouse

  DOI：10.1021/jacs.8b13127

  日期：2019.1.30

  We report the total syntheses of two indole diterpenoid natural products, paspaline A and emindole PB. Paspaline A is synthesized in a 9-step sequence from commercially available materials. The first total synthesis of emindole PB is accomplished in 13 steps and confirms a previously ambiguous structural assignment. Density functional theory calculations are utilized to interrogate the key carbocationic rearrangement in a predictive capacity to aid in the selection of the most favorable precursor substrate. This work highlights how retro-synthetic design can be augmented with quantum chemical calculations to reveal energetically feasible synthetic disconnections, minimizing time-consuming and expensive empirical evaluation.