20-epi-ervatamine | 33495-49-7

• 分子结构分类: 有机化合物 - 生物碱及其衍生物
• 英文名称: 20-epi-ervatamine
• 英文别名: methyl (3R,7R,8S)-7-ethyl-5-methyl-10-oxo-5,12-diazatetracyclo[9.7.0.03,8.013,18]octadeca-1(11),13,15,17-tetraene-3-carboxylate
• CAS: 33495-49-7
• 化学式: C₂₁H₂₆N₂O₃
• 分子量: 354.449
• InChiKey: METLQVFFFUYXNT-PCMMCCAGSA-N

物化性质

• 沸点：
  506.6±50.0 °C(Predicted)
• 密度：
  1?+-.0.06 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  62.4
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[5-acetyl-4-[2-(1-benzylindol-2-yl)-2-oxoethyl]-1-methyl-4H-pyridin-3-yl]-2,2,2-trichloroethanone 在 platinum(IV) oxide manganese(IV) oxide 、 三氯化铝 、 偶氮二异丁腈 、 氢气 、 三正丁基氢锡 、 三乙基硼氢化锂 、 sodium cyanoborohydride 、 三乙胺 、 lithium chloride 、 碘甲烷 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 氯仿 、 丙酮 、 苯 为溶剂， 反应 27.1h， 生成 20-epi-ervatamine
  参考文献：
  名称：

  Biomimetic Total Synthesis of Ervitsine and Indole Alkaloids of the Ervatamine Group via 1,4-Dihydropyridines

  摘要：

  Addition of the enolate derived from 2-acetylindole In to pyridinium salt 2 followed by in situ trapping of the initially formed 1,4-dihydropyridine 3a with Eschenmoser's salt gives tetracycle 5a. Subsequent elaboration of the exocyclic methylene and E-ethylidene substituents leads to N-a-methylervitsine (17a). A similar sequence from the N-a-protected 2-acetylindole Ic establishes the first total synthesis of the 2-acylindole alkaloid ervitsine. Alternatively, dihydropyridine 3a is trapped with BrSePh to give the tetracyclic selenide 7a, which is then converted to N-a-methylervitsine by way of selenoxide 20. The synthesis of the alkaloids of the ervatamine group starts with the addition of the enolate derived from 2-acetyl-1-benzylindole (Ig) to pyridinium salt 24 and the conversion of the resulting 1,4-dihydropyridine to 3,5-diacylated dihydropyridine 26g. Chemoselective reduction of the vinylogous amide moiety of 26g, followed by deprotection of the indole ring and LiEt3BH reduction leads to diol 37b. On sequential treatment with Eschenmoser's salt, methyl iodide, NaCNBH3, and MnO2, 37b is converted to the tetracyclic 2-acylindole 39, from which the first total synthesis of 19,20-didehydroervatamine and 20-epiervatamine is accomplished by manipulation of the l-hydroxyethyl chain. The above syntheses can be considered as biomimetic, as cyclization of the key intermediates I and II mimics the key steps of the biosynthesis of the title alkaloids.

  DOI：

  10.1021/jo9623301

文献信息

• Total Synthesis of Indole Alkaloids of the Ervatamine Group. A Biomimetic Approach
  作者：M.-Lluïsa Bennasar、Bernat Vidal、Joan Bosch

  DOI：10.1021/jo9600058

  日期：1996.1.1
• Rearrangement of vobasine to ervatamine-type alkaloids catalyzed by liver microsomes
  作者：C. Thal、M. Dufour、P. Potier、M. Jaouen、D. Mansuy

  DOI：10.1021/ja00406a055

  日期：1981.8