(rel-1S,3aS,4R,5R,7S,8R,8aS)-5-{[(1H-imidazol-1-yl)sulfonyl]oxy}-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (rel-1S,3aS,4R,5R,7S,8R,8aS)-5-{[(1H-imidazol-1-yl)sulfonyl]oxy}-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate
• 英文别名: [(1S,2R,5R,6R,7S,8R,10S)-10-imidazol-1-ylsulfonyloxy-1,5-dimethyl-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-7-yl] (E)-3-phenylprop-2-enoate
• 化学式: C₂₇H₃₄N₂O₆S
• 分子量: 514.643
• InChiKey: FFLHAUZAEWAQCF-DVPJTDQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5
• 重原子数：
  36
• 可旋转键数：
  8
• 环数：
  5.0
• sp3杂化的碳原子比例：
  0.56
• 拓扑面积：
  105
• 氢给体数：
  0
• 氢受体数：
  7

反应信息

• 作为反应物：
  描述：

  (rel-1S,3aS,4R,5R,7S,8R,8aS)-5-{[(1H-imidazol-1-yl)sulfonyl]oxy}-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate 在 18-冠醚-6 、 potassium carbonate 作用下， 以 甲醇 、 甲苯 为溶剂， 反应 37.0h， 生成 (-)-englerin B
  参考文献：
  名称：

  A Brief Synthesis of (−)-Englerin A

  摘要：

  Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic centers, including a highly unusual glycolate residue. Englerin A is a potent and selective inhibitor of the growth of six human renal cancer cell lines. We report herein an efficient, eight-step synthesis of englerin A that leverages simple carbonyl-enabled carbon carbon bond formations. Our route is amenable to the production of a diverse series of analogues for structure function studies and determination of the mode of action of these natural products.

  DOI：

  10.1021/ja201921j
• 作为产物：
  描述：

  [(1S,2R,5R,6R,7S,8R)-1,5-dimethyl-10-oxo-8-propan-2-yl-11-oxatricyclo[6.2.1.02,6]undecan-7-yl] (E)-3-phenylprop-2-enoate 在 sodium tetrahydroborate 、 正丁基锂 、 六甲基二硅氮烷 作用下， 以 四氢呋喃 、 甲醇 为溶剂， 反应 42.0h， 生成 (rel-1S,3aS,4R,5R,7S,8R,8aS)-5-{[(1H-imidazol-1-yl)sulfonyl]oxy}-7-isopropyl-1,4-dimethyldecahydro-4,7-epoxyazulen-8-yl cinnamate
  参考文献：
  名称：

  A Brief Synthesis of (−)-Englerin A

  摘要：

  Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic centers, including a highly unusual glycolate residue. Englerin A is a potent and selective inhibitor of the growth of six human renal cancer cell lines. We report herein an efficient, eight-step synthesis of englerin A that leverages simple carbonyl-enabled carbon carbon bond formations. Our route is amenable to the production of a diverse series of analogues for structure function studies and determination of the mode of action of these natural products.

  DOI：

  10.1021/ja201921j

文献信息

• Total Synthesis of (±)-Englerin A and Its Tuncated Analogues
  作者：Colleen Reagan、Graham Trevitt、Kirill Tchabanenko

  DOI：10.1002/ejoc.201801544

  日期：2019.2.7

  Total synthesis of (±)‐Englerin A and a number of truncated analogues was developed based on a 1,3‐dipolar cycloaddition of a substituted pyrylium ylide. The bicyclic enone scaffold was further converted into a truncated analogue and the natural product. Interesting stereochemical effects of the bridgehead substituents on the reactivity of the 8‐oxabicyclo[3.2.1]octanes were uncovered.

  基于取代的吡啶鎓叶立德的1,3-偶极环加成反应，开发了（±）-Englerin A和许多截短的类似物的全合成。将双环烯酮支架进一步转化为截短的类似物和天然产物。桥头取代基对8-氧杂双环[3.2.1]辛烷的反应性的有趣的立体化学作用被发现。
• A Brief Synthesis of (−)-Englerin A
  作者：Zhenwu Li、Mika Nakashige、William J. Chain

  DOI：10.1021/ja201921j

  日期：2011.5.4

  Englerins A and B are guaiane sesquiterpenes that were isolated from the bark of Phyllanthus engleri, a plant indigenous to east Africa. The englerins consist of a 5-6-5 fused tricyclic structure with an ether bridge and two ester-bearing stereogenic centers, including a highly unusual glycolate residue. Englerin A is a potent and selective inhibitor of the growth of six human renal cancer cell lines. We report herein an efficient, eight-step synthesis of englerin A that leverages simple carbonyl-enabled carbon carbon bond formations. Our route is amenable to the production of a diverse series of analogues for structure function studies and determination of the mode of action of these natural products.