(5S,11bR)-11-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxo-2,5,6,11b-tetrahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid | 948909-17-9

• 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: (5S,11bR)-11-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxo-2,5,6,11b-tetrahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid
• CAS: 948909-17-9
• 化学式: C₂₀H₂₂N₂O₅
• 分子量: 370.405
• InChiKey: QWVJHPYWTSOQRG-CABCVRRESA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.4
• 重原子数：
  27
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.45
• 拓扑面积：
  88.8
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (5S,11bR)-11-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxo-2,5,6,11b-tetrahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid 在 三丁基膦 、 二苯基二硒醚 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 22.0h， 生成 (R)-1,2,5,6,11,11b-hexahydro-3H-indolizino[8,7-b]indol-3-one
  参考文献：
  名称：

  A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7-b]indole alkaloid (+)-harmicine

  摘要：

  We report a novel, facile and asymmetric approach for the synthesis of the indole alkaloid (+)-harmicine via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step, and verify the relative stereochemistry of the key synthetic intermediate in this approach through X-ray crystallography. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.034
• 作为产物：
  描述：

  1-[(S)-1-Hydroxymethyl-2-(1H-indol-3-yl)-ethyl]-pyrrolidine-2,5-dione 在 4-二甲氨基吡啶 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium dihydrogenphosphate 、 二甲基亚砜 、 三乙胺 、 环己烯 、 2-碘酰基苯甲酸 作用下， 以 四氢呋喃 、 乙醇 、 乙腈 、 叔丁醇 为溶剂， 反应 46.0h， 生成 (5S,11bR)-11-[(2-methylpropan-2-yl)oxycarbonyl]-3-oxo-2,5,6,11b-tetrahydro-1H-indolizino[8,7-b]indole-5-carboxylic acid
  参考文献：
  名称：

  A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7-b]indole alkaloid (+)-harmicine

  摘要：

  We report a novel, facile and asymmetric approach for the synthesis of the indole alkaloid (+)-harmicine via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step, and verify the relative stereochemistry of the key synthetic intermediate in this approach through X-ray crystallography. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2007.06.034

文献信息

• Selective Deconstructive Lactamization of the Indolo[2,3‐ <i>a</i> ]quinolizine Skeleton for the Total Synthesis of (+) and (−)‐Cuscutamine
  作者：Adriana Recoba‐Torres、Silvano Cruz‐Gregorio、Leticia Quintero、Jacinto Sandoval‐Lira、Julio Romero‐Ibañez、Fernando Sartillo‐Piscil

  DOI：10.1002/ejoc.202200292

  日期：2022.8.26

  A selective deconstructive strategy of indolo[2,3-a]quinolizines to hexahydroindolizin-3-ones under transition-metal-free conditions was developed and applied to the total synthesis of both enantiomers of cuscutamine. Additionally, controversy of the absolute configuration of the natural products was clarified.

  开发了一种在无过渡金属条件下将吲哚[2,3- a ]喹啉选择性解构为六氢吲哚嗪-3-酮的策略，并将其应用于菟丝子胺两种对映异构体的全合成。此外，澄清了天然产物绝对构型的争议。
• A new asymmetric synthesis of the natural enantiomer of the indolizidino[8,7-b]indole alkaloid (+)-harmicine
  作者：Steven M. Allin、Sean N. Gaskell、Mark R.J. Elsegood、William P. Martin

  DOI：10.1016/j.tetlet.2007.06.034

  日期：2007.8

  We report a novel, facile and asymmetric approach for the synthesis of the indole alkaloid (+)-harmicine via a highly diastereoselective N-acyliminium cyclization reaction as a key synthetic step, and verify the relative stereochemistry of the key synthetic intermediate in this approach through X-ray crystallography. Crown Copyright (c) 2007 Published by Elsevier Ltd. All rights reserved.