(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 | 159333-19-4

• 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: (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
• CAS: 159333-19-4
• 化学式: C₂₆H₃₆N₂O₆
• 分子量: 472.582
• InChiKey: MHXXQPUXXRWOSX-STTRJGPESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.3
• 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：
  96.4
• 氢给体数：
  1
• 氢受体数：
  6

反应信息

• 作为反应物：
  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 碘代三甲硅烷 、 双(2-氧代-3-恶唑烷基)次磷酰氯 、 三乙胺 作用下， 以 二氯甲烷 、 乙腈 为溶剂， 生成 苯(甲)醛,4-(1-甲基乙基)-,2-亚甲基腙
  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：

  L-色氨酸甲酯 在 sodium hydroxide 、 2,6-二叔丁基吡啶 、 四丁基硫酸氢铵 、 4-甲基苯磺酸吡啶 、 三氟甲烷磺酸甲酯 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 生成 (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
  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

• Total synthesis of isoroquefortine E and phenylahistin
  作者：Ning Shangguan、Madeleine M. Joullié

  DOI：10.1016/j.tetlet.2009.09.074

  日期：2009.12

  Isoroquefortine E and phenylahistin were synthesized using the Horner-Wadsworth-Emmons reaction as the key step to build the dehydroamino acid moiety. The syntheses provided the materials for the biological studies of the roquefortine-phenylahistin molecules. (C) 2009 Elsevier Ltd. All rights reserved.
• 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
• Synthesis of Brevicompanines, Plant Growth Regulators
  作者：Takeshi Kitahara、Koji Matsumura

  DOI：10.3987/com-00-s(i)51

  日期：——
• The Total Synthesis of Roquefortine C and a Rationale for the Thermodynamic Stability of Isoroquefortine C over Roquefortine C
  作者：Ning Shangguan、Warren J. Hehre、William S. Ohlinger、Mary Pat Beavers、Madeleine M. Joullié

  DOI：10.1021/ja800067q

  日期：2008.5.1

  The first total synthesis of roquefortine C is achieved by implementation of a novel elimination strategy to construct the thermodynamically unstable E-dehydrohistidine moiety. Molecular modeling studies are presented which explain the instability of the roquefortine C structure compared to that of isoroquefortine C.
• The first total synthesis of roquefortine D
  作者：Wei-Chuan Chen、Madeleine M. Joullié

  DOI：10.1016/s0040-4039(98)01957-1

  日期：1998.11

  The synthesis of roquefortine D (1), an alkaloid isolated from the cultures of Penicillium roqueforti, is described. The absolute stereochemistry of the natural product was determined by comparison of its optical rotation with that of the synthetic product. A photo-cleavable o-nitrobenzyl group was utilized for histidine side chain protection, and the cyclisation to the diketopiperazine was carried out under mild conditions. (C) 1998 Elsevier Science Ltd. All rights reserved.