(1S,3S)-methyl 1-(3-acetoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate | 1223077-64-2

• 分子结构分类: 有机化合物 - 生物碱及其衍生物 - 哈马拉生物碱
• 英文名称: (1S,3S)-methyl 1-(3-acetoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1223077-64-2
• 化学式: C₂₁H₂₀N₂O₄
• 分子量: 364.401
• InChiKey: DRSFVCNEVMDIOD-OALUTQOASA-N

反应信息

• 作为产物：
  描述：

  在 碳酸氢钠 作用下， 以 硝基甲烷 、 甲苯 、 水 、 乙酸乙酯 为溶剂， 反应 12.0h， 以95%的产率得到(1S,3S)-methyl 1-(3-acetoxyphenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
  参考文献：
  名称：

  The first highly stereoselective approach to the mitotic kinesin Eg5 inhibitor HR22C16 and its analogues

  摘要：

  A general method for the synthesis of the mitotic kinesin Eg5 inhibitor HR22C16 1 and its analogues based on protecting group (PG)-modulated highly diastereoselective Pictet-Spengler reaction of L-tryptophan methyl ester hydrochloride with meta-(RO)-benzaldehyde is described. By using the enantiomerically pure (1R,3S)-1,3-disubstituted tetrahydro-beta-carboline trans-4c as a common chiral synthon, HR22C16 1 and its analogues 2 and 3 were synthesized in 90.1%, 90.2%, and 86.5% overall yields, respectively. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2009.12.029