(+)-madindoline A | 302812-74-4

• 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: (+)-madindoline A
• 英文别名: (2R)-2-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-butyl-2,5-dimethylcyclopent-4-ene-1,3-dione
• CAS: 302812-74-4
• 化学式: C₂₈H₄₁NO₄Si
• 分子量: 483.723
• InChiKey: JAWYBYHKCLAJOD-KJYTXNCISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.13
• 重原子数：
  34
• 可旋转键数：
  8
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.64
• 拓扑面积：
  55.8
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (+)-madindoline A 在 四丁基氟化铵 作用下， 以 四氢呋喃 为溶剂， 以64%的产率得到(+)-madindoline A
  参考文献：
  名称：

  Total synthesis of madindoline A

  摘要：

  The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)(2)-NaBH(OAc)(3). After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00939-4
• 作为产物：
  描述：

  (4R)-4-[[(3aS,8bR)-8b-[tert-butyl(dimethyl)silyl]oxy-2,3a-dihydro-1H-furo[2,3-b]indol-4-yl]methyl]-4-methyldecane-3,5,6-trione 在 1,8-二氮杂双环[5.4.0]十一碳-7-烯 作用下， 以 苯 为溶剂， 以87%的产率得到(+)-madindoline A
  参考文献：
  名称：

  Total synthesis of madindoline A

  摘要：

  The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)(2)-NaBH(OAc)(3). After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00939-4

文献信息

• Short Total Synthesis of (+)-Madindolines A and B
  作者：Tomoyasu Hirose、Toshiaki Sunazuka、Tatsuya Shirahata、Daisuke Yamamoto、Yoshihiro Harigaya、Isao Kuwajima、Satoshi Ōmura

  DOI：10.1021/ol017058i

  日期：2002.2.1

  A short and efficient total synthesis of (+)-madindolines A (1) and B (2), potent and selective inhibitors of interleukin 6, has been achieved. The synthesis features a key chelation-controlled 1,4-diastereoselective acylation to generate the quaternary carbon and an intramolecular acylation of allylsilane to build up the cyclopentene unit.
• Total synthesis of madindoline A
  作者：Seijiro Hosokawa、Kazuhiko Sekiguchi、Kanako Hayase、Yasushi Hirukawa、Susumu Kobayashi

  DOI：10.1016/s0040-4039(00)00939-4

  日期：2000.8

  The total synthesis of madindoline A was achieved. The key step of the synthesis is a reductive coupling of an acid-sensitive hydroxyfuroindoline derivative and a sterically hindered aldehyde using Sn(OTf)(2)-NaBH(OAc)(3). After the reductive coupling, the derived trione was subjected to intramolecular condensation to construct a madindoline skeleton. (C) 2000 Elsevier Science Ltd. All rights reserved.