methyl (1S,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate | 1443051-72-6

• 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: methyl (1S,3S)-1-((R)-2,2-dimethyl-1,3-dioxolan-4-yl)-1,2,3,4-tetrahydro-9H-pyrido[3,4-b]indole-3-carboxylate
• 英文别名: methyl (1S,3S)-1-[(4R)-2,2-dimethyl-1,3-dioxolan-4-yl]-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate
• CAS: 1443051-72-6
• 化学式: C₁₈H₂₂N₂O₄
• 分子量: 330.384
• InChiKey: UCVLEOQGUFDENX-OFQRWUPVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.7
• 重原子数：
  24
• 可旋转键数：
  3
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  72.6
• 氢给体数：
  2
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  L-甘油醛缩丙酮 、 L-色氨酸甲酯 在 三氟乙酸 作用下， 以 乙酸乙酯 为溶剂， 反应 5.17h， 以30%的产率得到
  参考文献：
  名称：

  Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality

  摘要：

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetasy.2013.04.009

文献信息

• Novel asymmetric total syntheses of (R)-(−)-pyridindolol, (R)-(−)-pyridindolol K1, and (R)-(−)-pyridindolol K2 via a mild one-pot aromatization of N-tosyl-tetrahydro-β-carboline with (S)-2,3-O-isopropylidene-l-glyceraldehyde as the source of chirality
  作者：Qiang Zhang、Zhen Fan、Jing Dong、Xiao-Xin Shi、Xia Lu

  DOI：10.1016/j.tetasy.2013.04.009

  日期：2013.6

  Novel total syntheses of (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 are described. By using L-tryptophan methyl ester and (S)-2,3-O-isopropylidene-L-glyceraldehyde as the starting materials, (R)-(-)-pyridindolol 1, (R)-(-)-pyridindolol K1 2, and (R)-(-)-pyridindolol K2 3 were synthesized in 5-7 steps in 66%, 41%, and 55% overall yields, respectively. The characteristic step of the total syntheses is a mild one-pot aromatization of N-tosyl-1,2,3,4-tetrahydro-beta-carboline (N-Ts-THBC), which was obtained via Pictet-Spengler reaction of L-tryptophan methyl ester with (S)-2,3-O-isopropylidene-L-glyceraldehyde, and subsequent N-tosylation. (C) 2013 Elsevier Ltd. All rights reserved.