ditert-butyl (2S,3aR,8bR)-2-carbonofluoridoyl-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate | 258883-28-2

• 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-carbonofluoridoyl-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate
• CAS: 258883-28-2
• 化学式: C₂₆H₃₅FN₂O₅
• 分子量: 474.573
• InChiKey: XBWDSSAFZKBVSF-STTRJGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  34
• 可旋转键数：
  7
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.58
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  ditert-butyl (2S,3aR,8bR)-2-carbonofluoridoyl-8b-(2-methylbut-3-en-2-yl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-3,4-dicarboxylate 在 4-二甲氨基吡啶 、 碘代三甲硅烷 、 氨 、 碳酸氢钠 作用下， 以 甲醇 、 二氯甲烷 、 水 、 乙腈 为溶剂， 生成 (2S,3aR,8bR)-N-[(2R)-1-amino-1-oxopropan-2-yl]-8b-(2-methylbut-3-en-2-yl)-2,3,3a,4-tetrahydro-1H-pyrrolo[2,3-b]indole-2-carboxamide
  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
• 作为产物：
  描述：

  (2S,3aR,8bR)-8b-(2-methylbut-3-en-2-yl)-3,4-bis[(2-methylpropan-2-yl)oxycarbonyl]-2,3a-dihydro-1H-pyrrolo[2,3-b]indole-2-carboxylic acid 在 吡啶 、 三聚氟氰 作用下， 以 二氯甲烷 为溶剂， 以93%的产率得到ditert-butyl (2S,3aR,8bR)-2-carbonofluoridoyl-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

文献信息

• ANALOGUES OF N-ACETYLARDEEMIN, METHOD OF PREPARATION AND USES THEREOF
  申请人：The Trustees of Columbia University in the City of New York

  公开号：EP0815111B1

  公开（公告）日：2007-10-10
• Stereoselective Total Syntheses of Amauromine and 5-N-Acetylardeemin. A Concise Route to the Family of "Reverse-Prenylated" Hexahydropyrroloindole Alkaloids
  作者：Stephen P. Marsden、Kristopher M. Depew、Samuel J. Danishefsky

  DOI：10.1021/ja00103a034

  日期：1994.11