(-)-1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-oxo-3,3'-biindolin-1,1',3-tricarboxylate | 1290053-12-1

• 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: (-)-1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-oxo-3,3'-biindolin-1,1',3-tricarboxylate
• 英文别名: 1-O-tert-butyl 3-O-(1,1,1-trichloro-2-methylpropan-2-yl) (3R)-3-[1-[(2-methylpropan-2-yl)oxycarbonyl]indol-3-yl]-2-oxoindole-1,3-dicarboxylate
• CAS: 1290053-12-1
• 化学式: C₃₁H₃₃Cl₃N₂O₇
• 分子量: 651.971
• InChiKey: AOTQUSLGPVNUQD-PMERELPUSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  7.5
• 重原子数：
  43
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.42
• 拓扑面积：
  104
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (-)-1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-oxo-3,3'-biindolin-1,1',3-tricarboxylate 在 sodium tetrahydroborate 作用下， 以 甲醇 为溶剂， 反应 1.0h， 生成 1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-hydroxy-3,3'-biindoline-1,1',3-tricarboxylate 、 1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-hydroxy-3,3'-biindoline-1,1',3-tricarboxylate
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

  摘要：

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

  DOI：

  10.1021/ja201789v
• 作为产物：
  描述：

  3-hydroxy-3-indolyl-2-oxindole 在 三乙基硅烷 、 4-二甲氨基吡啶 、 (S)-(-)-4-pyrrolidinopyridinyl(pentamethylcyclopentadienyl)iron 、 三乙胺 、 三氟乙酸 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 88.0h， 生成 (-)-1,1'-di-tert-butyl 3-(1,1,1-trichloro-2-methylpropan-2-yl) 2-oxo-3,3'-biindolin-1,1',3-tricarboxylate
  参考文献：
  名称：

  Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors

  摘要：

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.

  DOI：

  10.1021/ja201789v

文献信息

• Enantioselective Total Synthesis of (+)-Gliocladine C: Convergent Construction of Cyclotryptamine-Fused Polyoxopiperazines and a General Approach for Preparing Epidithiodioxopiperazines from Trioxopiperazine Precursors
  作者：John E. DeLorbe、Salman Y. Jabri、Steven M. Mennen、Larry E. Overman、Fang-Li Zhang

  DOI：10.1021/ja201789v

  日期：2011.5.4

  A concise second-generation total synthesis of the fungal-derived alkaloid (+)-gliocladin C (11) in 10 steps and 1196 overall yield from isatin is reported. In addition, the epipolythiodioxopiperazine (ETP) natural product (+)-gliocladine C (6) has been prepared in six steps and 2996 yield from the di-(tert-butoxycarbonyl) precursor of 11. The total synthesis of 6 constitutes the first total synthesis of an ETP natural product containing a hydroxyl substituent adjacent to a quaternary carbon stereocenter in the pyrrolidine ring.