(+/-)-1-methyl-3a-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole

• 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-methyl-3a-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
• 英文别名: (+/-)-debromoflustramine A；debromoflustramine A；(3aR,8bR)-3-methyl-8b-(2-methylbut-3-en-2-yl)-4-(3-methylbut-2-enyl)-2,3a-dihydro-1H-pyrrolo[2,3-b]indole
• 化学式: C₂₁H₃₀N₂
• 分子量: 310.483
• InChiKey: CEIMOFSBIPXHIA-TZIWHRDSSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  6.5
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为产物：
  描述：

  ethyl 2-(1H-indole-3-yl)ethylcarbamate 在 1,4-二甲基哌嗪 、 4-二甲氨基吡啶 、 N-氯代丁二酰亚胺 、 lithium aluminium tetrahydride 、 alane N,N-dimethylethylamine complex 、 sodium hydride 、 caesium carbonate 、 苯硫酚 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 甲苯 、 mineral oil 为溶剂， 反应 7.75h， 生成 (+/-)-1-methyl-3a-(2-methylbut-3-en-2-yl)-8-(3-methylbut-2-enyl)-1,2,3,3a-tetrahydropyrrolo[2,3-b]indole
  参考文献：
  名称：

  Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy

  摘要：

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2011.01.020

文献信息

• Total Synthesis of (±)-Flustramines A and C, (±)-Flustramide A, and (−)- and (+)-Debromoflustramines A
  作者：Tomomi Kawasaki、Masashi Shinada、Mayu Ohzono、Atsuyo Ogawa、Romi Terashima、Masanori Sakamoto

  DOI：10.1021/jo800984a

  日期：2008.8.1

  derivative from readily available indolin-3-ones using key domino reactions, olefination−isomerization−Claisen rearrangement (OIC), and reductive cyclization (RC). (±)-Flustramine C (5) was synthesized in five steps from 6-bromoindolin-3-one 9 via a key intermediate 13a. (±)-Flustramine A (1) has been obtained by reduction of flustramide A (6), which has been prepared in five steps from 13a. (±)-Debromoflustramine

  在这里，我们描述了三个关键的六氢吡咯并[2,3- b ]吲哚生物碱和十溴衍生物的有效全合成，这些衍生物使用关键的多米诺反应，烯化-异构化-克莱森重排（OIC）和还原性环化反应从容易获得的吲哚-3-酮中合成（RC）。（±）-氟胺C（5）由6-溴吲哚-3-酮9经关键中间体13a分五步合成。（±）-氟他胺A（1）已通过从13a的五个步骤制备的氟他胺A（6）还原获得。以类似于13b的方式提供了（±）-去溴氟胺A（19）。使用（R）-4-苯基恶唑烷二-2-酮，通过（±）-羧酸17b的光学拆分，合成了19的（-）-和（+）-对映体。
• Catalytic Asymmetric Reverse Prenylation of Indol-2-one Enabled a Synthesis of (−)-Debromoflustramine A
  作者：Yi Hou、Jiyou Huo、Ruoxin Li、Jun Hou、Pan Lei、Hongbo Wei、Weiqing Xie

  DOI：10.1021/acs.orglett.3c02296

  日期：2023.9.29

  A catalytic asymmetric nucleophilic reverse prenylation of indol-2-ones in situ generated from 3-bromooxindoles with prenyltributylstannane promoted by Ni(II)/chiral N,N′-dioxide was developed. This reaction provides facile access to C3 reverse-prenylated oxindoles in good to excellent enantioselectivities, which enabled the asymmetric synthesis of debromoflustramine A in five steps.

  开发了由 Ni(II)/手性N,N'-二氧化物促进的异戊烯基三丁基锡烷对 3-溴氧吲哚产生的吲哚-2-酮原位催化不对称亲核反异戊二烯化反应。该反应以良好至优异的对映选择性方便地获得 C3 反向异戊二烯化羟吲哚，从而能够通过五个步骤不对称合成去溴氟曲明 A。
• General Approach to the Synthesis of Marine Bryozoan <i>Flustra foliacea</i> Alkaloids:  Total Syntheses of Debromoflustramines A and B
  作者：Martha S. Morales-Ríos、Oscar R. Suárez-Castillo、Pedro Joseph-Nathan

  DOI：10.1021/jo982090k

  日期：1999.2.1
• Step-economic synthesis of (±)-debromoflustramine A using indole C3 activation strategy
  作者：Vasily A. Ignatenko、Ping Zhang、Rajesh Viswanathan

  DOI：10.1016/j.tetlet.2011.01.020

  日期：2011.3

  A concise and practical strategy to obtain C3 reverse-prenylated pyrrolidinoindoline scaffold has been executed in 28.8% overall yield. The key conjugative step involved a Booker-Milburn-Feudoloff reaction involving an NCS-mediated activation of indole, followed by coupling to C(5) dimethylallylalcohol. This linchpin step proceeded in 74% yield. The overall sequence proceeded in five steps from commercially available N-methyltryptamine with a single protection-deprotection operation and a single redox manipulation. Mechanistic insights of NCS activation, and an ensuing rearrangement of the isoprene unit were gained by rationally varying the C3 substituent. (C) 2011 Elsevier Ltd. All rights reserved.

表征谱图