8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester | 55528-28-4

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 冬青素型生物碱
• 英文名称: 8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester
• 英文别名: methyl (1R,12S,19S)-12-ethyl-15-sulfanylidene-8,16-diazapentacyclo[10.6.1.01,9.02,7.016,19]nonadeca-2,4,6,9-tetraene-10-carboxylate
• CAS: 55528-28-4
• 化学式: C₂₁H₂₄N₂O₂S
• 分子量: 368.5
• InChiKey: DJTZPINZTWICAF-ACRUOGEOSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  26
• 可旋转键数：
  3
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  73.7
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester 在 镍 作用下， 以 乙醇 为溶剂， 反应 16.0h， 以87%的产率得到(-)-vincadifformine
  参考文献：
  名称：

  Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids:  Enantioselective Syntheses of Vincadifformine, ψ- and 20-epi-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine

  摘要：

  Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7,14a and 14b,21a,c and 21b,d,30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (-)-psi- and (-)-epi-psi-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)-and (-)-vincadifformine (16a, 16b), (-)-tabersonine (27), and (-)-mossambine (41).

  DOI：

  10.1021/jo971838g
• 作为产物：
  描述：

  3-oxovincadifformine 在 tetraphosphorus decasulfide 作用下， 以 四氢呋喃 为溶剂， 反应 19.0h， 生成 8-thioxo-2,3-didehydro-aspidospermidine-3-carboxylic acid methyl ester
  参考文献：
  名称：

  Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids:  Enantioselective Syntheses of Vincadifformine, ψ- and 20-epi-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine

  摘要：

  Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7,14a and 14b,21a,c and 21b,d,30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (-)-psi- and (-)-epi-psi-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)-and (-)-vincadifformine (16a, 16b), (-)-tabersonine (27), and (-)-mossambine (41).

  DOI：

  10.1021/jo971838g

文献信息

• Application of Ferrocenylalkyl Chiral Auxiliaries to Syntheses of Indolenine Alkaloids:  Enantioselective Syntheses of Vincadifformine, ψ- and 20-<i>epi</i>-ψ-Vincadifformines, Tabersonine, Ibophyllidine, and Mossambine
  作者：Martin E. Kuehne、Upul K. Bandarage、Abdelhakim Hammach、Yun-Long Li、Tiansheng Wang

  DOI：10.1021/jo971838g

  日期：1998.4.1

  Condensations of the chiral N-ferrocenylethylindoloazepines 4a,b, with the aldehydes 5, 13, 19, 29, and 32, led to tetracyclic vinylogous urethanes 6a,b and 7,14a and 14b,21a,c and 21b,d,30a and 31a, and 30b and 31b. Respectively, 6:1, 5:1, 3:1, 1.7:1, and 2:1 diastereomeric selections provided intermediates which, on cleavage of the chiral auxiliary N-substituent and subsequent elaboration of ring D of the Aspidosperma and Strychnos alkaloids, provided enantiomerically pure (-)-psi- and (-)-epi-psi-vincadifformines (1, 2), (+)-ibophyllidine (12), (+)-and (-)-vincadifformine (16a, 16b), (-)-tabersonine (27), and (-)-mossambine (41).