deisobutyryl garsubellin A

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: deisobutyryl garsubellin A
• 英文别名: (1R,3R,8R,10R)-3-(2-hydroxypropan-2-yl)-9,9-dimethyl-6,10-bis(3-methylbut-2-enyl)-4-oxatricyclo[6.3.1.01,5]dodec-5-ene-7,12-dione
• 化学式: C₂₆H₃₈O₄
• 分子量: 414.585
• InChiKey: YMBCHAVECJAKHD-RKZHYGFVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  30
• 可旋转键数：
  5
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.69
• 拓扑面积：
  63.6
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  deisobutyryl garsubellin A 在 异丙基氯化镁 、 戴斯-马丁氧化剂 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 乙醚 、 二氯甲烷 为溶剂， 反应 4.84h， 生成 (1S,3S,8R,10S)-8-Isobutyryl-9,9-dimethyl-6,10-bis-(3-methyl-but-2-enyl)-3-(1-methyl-1-trimethylsilanyloxy-ethyl)-4-oxa-tricyclo[6.3.1.0^1,5]dodec-5-ene-7,12-dione
  参考文献：
  名称：

  Total Synthesis of Garsubellin A

  摘要：

  A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.

  DOI：

  10.1021/ja057418n
• 作为产物：
  描述：

  (1R,3S,8S,10S)-6-Allyl-3-(1-hydroxy-1-methyl-ethyl)-10-iodo-9,9-dimethyl-4-oxa-tricyclo[6.3.1.0^1,5]dodec-5-ene-7,12-dione 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 、 偶氮二异丁腈 作用下， 以 二氯甲烷 、 苯 为溶剂， 反应 26.0h， 生成 deisobutyryl garsubellin A
  参考文献：
  名称：

  Total Synthesis of Garsubellin A

  摘要：

  A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.

  DOI：

  10.1021/ja057418n

文献信息

• Total Synthesis of Garsubellin A
  作者：Dionicio R. Siegel、Samuel J. Danishefsky

  DOI：10.1021/ja057418n

  日期：2006.2.1

  A concise approach to the laboratory synthesis of garsubellin A is described. Garsubellin A, an effective inducer of choline acetyltransferase (ChAT), has been shown to have potential as a therapeutic agent for the treatment of Alzheimer's disease. Starting from 3,5-dimethoxyphenol, the synthesis has provided garsubellin A in an 18-step sequence. Notable transformations include dearomative allylation, diastereoselective vinylogous lactonization, iodocarbocyclization, transannular Wurtz, and bridgehead functionalization reactions.