ditert-butyl (2S,3aR,8bR)-2-[(2S,3aS,8bR)-2-methoxycarbonyl-8b-(2-methylbut-3-en-2-yl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carbonyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate | 159333-21-8

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: ditert-butyl (2S,3aR,8bR)-2-[(2S,3aS,8bR)-2-methoxycarbonyl-8b-(2-methylbut-3-en-2-yl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carbonyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
• CAS: 159333-21-8
• 化学式: C₄₃H₅₆N₄O₇
• 分子量: 740.94
• InChiKey: ZVIHEOWTVUPDDB-XLHBUUOPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  9
• 重原子数：
  54
• 可旋转键数：
  11
• 环数：
  6.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  118
• 氢给体数：
  1
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S,3aR,8bR)-2-[(2S,3aS,8bR)-2-methoxycarbonyl-8b-(2-methylbut-3-en-2-yl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carbonyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate 在 碘代三甲硅烷 作用下， 以 乙腈 为溶剂， 以98%的产率得到amauromine
  参考文献：
  名称：

  Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids

  摘要：

  DOI：

  10.1021/ja00103a034
• 作为产物：
  描述：

  (2S,3aR,8aR)-1,8-ditert-butyl 2-methyl 3a-(2-methylbut-3-en-2-yl)-3,3a-dihydropyrrolo[2,3-b]indole-1,2,8(2H,8aH)-tricarboxylate 在 sodium hydroxide 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 ditert-butyl (2S,3aR,8bR)-2-[(2S,3aS,8bR)-2-methoxycarbonyl-8b-(2-methylbut-3-en-2-yl)-1,2,3a,4-tetrahydropyrrolo[2,3-b]indole-3-carbonyl]-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
  参考文献：
  名称：

  Total Synthesis of 5-N-Acetylardeemin and Amauromine:  Practical Routes to Potential MDR Reversal Agents

  摘要：

  The total synthesis of the title compounds has been accomplished. The key step involves the kinetic stereoselective conversion of 19 --> 20. The synthesis of 20 represents for the first time a direct method for constructing exo-pyrroloindoles from protected tryptophans in a highly diastereoselective manner. This step was followed by reverse prenylation (see conversion of 20 --> 27). Using the methodology worked out for the titled compounds, a practical synthesis of several promising MDR reversal agents was possible. Biological data that provided the basis for selection of candidates for advanced study are presented. Preliminary profiling of the zones of the molecules that are responsive to changes while still retaining MDR reversal ability are described. On the basis of these findings, compounds 2, 50, and 51 were selected for more extensive biological follow-up.

  DOI：

  10.1021/ja991558d