(2S,3R,4aS,5S,8aR)-1-(tert-butoxycarbonyl)-2-methyl-3-hydroxy-5-[(5R)-5-(methoxymethoxy)octan-1-yl]decahydroquinoline | 782498-37-7

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 喹啉类
• 英文名称: (2S,3R,4aS,5S,8aR)-1-(tert-butoxycarbonyl)-2-methyl-3-hydroxy-5-[(5R)-5-(methoxymethoxy)octan-1-yl]decahydroquinoline
• CAS: 782498-37-7
• 化学式: C₂₅H₄₇NO₅
• 分子量: 441.652
• InChiKey: UEQZTMXXEYSPNV-OGXDUAGGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.51
• 重原子数：
  31.0
• 可旋转键数：
  10.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.96
• 拓扑面积：
  68.23
• 氢给体数：
  1.0
• 氢受体数：
  5.0

反应信息

• 作为反应物：
  描述：

  (2S,3R,4aS,5S,8aR)-1-(tert-butoxycarbonyl)-2-methyl-3-hydroxy-5-[(5R)-5-(methoxymethoxy)octan-1-yl]decahydroquinoline 在 4-二甲氨基吡啶 、 盐酸-N-乙基-Nˊ-(3-二甲氨基丙基)碳二亚胺 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 12.0h， 生成 lepadin H
  参考文献：
  名称：

  Lepadins B，d，e和h的全合成；确定后三种生物碱的构型。

  摘要：

  DOI：

  10.1002/anie.200460128
• 作为产物：
  描述：

  (R)-(-)-hexane-1,3-diol 在 palladium on activated charcoal 三丁基膦 、 四丁基氟化铵 、 氢气 、 sodium hexamethyldisilazane 、 碳酸氢钠 、 N,N-二异丙基乙胺 、 间氯过氧苯甲酸 、 偶氮二甲酸二乙酯 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 81.5h， 生成 (2S,3R,4aS,5S,8aR)-1-(tert-butoxycarbonyl)-2-methyl-3-hydroxy-5-[(5R)-5-(methoxymethoxy)octan-1-yl]decahydroquinoline
  参考文献：
  名称：

  Facile Entry to Substituted Decahydroquinoline Alkaloids. Total Synthesis of Lepadins A−E and H

  摘要：

  Condensation of a L-alanine derived delta-bromo-beta-silyloxy-propylamine with 1,3-cyclohexadione followed by alkylative cyclization produces a bicyclic enone. Diastereoselective Pt/C-catalyzed hydrogenation of this enone in HOAc provides a 5-oxo-cis-fused decahydroquinoline. Wittig olefination of this decahydroquinoline and subsequent epimerization of the resulting 5-formyl intermediate gives rise to a 5-beta-formyl decahydroquinoline exclusively. In a parallel procedure, Peterson reaction of this decahydroquinoline and subsequent hydrogenation of the generated 5-exo-olefin provides a decahydroquinoline with a 5-alpha-substituent predominantly. For these two diastereoselective processes, using the intermediates without N-protection as the substrates is essential because the corresponding N-Boc intermediates give poor diastereoselectivity. The intermediate with beta-form side chain is further converted into lepadins A-C via carbon chain elongation, while the intermediate with alpha-form side chain is transformed into lepadins D, E, and H and corresponding 5'-epimers via connection with two sulfones generated from two Sharpless epoxidation products. By comparison of the rotations and NMR data, the stereochemistry of lepadins D, E, and H is assigned as 2S, 3R, 4aS, 5S, 8aR, 5'R.

  DOI：

  10.1021/jo061070c

文献信息

• Collective Asymmetric Total Syntheses of Marine Decahydroquinoline Alkaloid Lepadins A–E, H, and <i>ent</i>-I
  作者：Foqing Ma、Chenxi He、Eryu Wang、Rongbiao Tong

  DOI：10.1021/acs.orglett.1c02435

  日期：2021.8.20

  Lepadins are cis-fused decahydroquinoline (DHQ) marine alkaloids that have shown diverse biological activities and have attracted extensive synthetic interest. A new collective synthetic strategy is reported that features a green chemistry approach for constructing the common cis-fused DHQ core, which is achieved through green oxone-halide oxidation for both the aza-Achmatowicz rearrangement and the

  Lepadins 是顺式融合的十氢喹啉 (DHQ) 海洋生物碱，具有多种生物活性并引起了广泛的合成兴趣。报道了一种新的集体合成策略，该策略采用绿色化学方法构建常见的顺式融合 DHQ 核心，这是通过绿色 oxone-卤化物氧化实现 aza-Achmatowicz 重排和腈的分子内 [3 + 2] 环加成氧化物-烯烃。lepadins A-E 和 H 的集体全合成是在 10 个步骤内从公共 DHQ 核心完成的。