(8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-hydroxybutylidene>octahydroindolizine | 138053-04-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚里西啶
• 英文名称: (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-hydroxybutylidene>octahydroindolizine
• CAS: 138053-04-0
• 化学式: C₂₀H₃₉NO₃Si
• 分子量: 369.62
• InChiKey: ARSMRDZIAPADTC-PRWXICMJSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.55
• 重原子数：
  25.0
• 可旋转键数：
  5.0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.9
• 拓扑面积：
  52.93
• 氢给体数：
  2.0
• 氢受体数：
  4.0

反应信息

• 作为反应物：
  描述：

  (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-hydroxybutylidene>octahydroindolizine 在 lithium aluminium tetrahydride 、 草酰氯 、 二甲基亚砜 、 三乙胺 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 74.33h， 生成 (+)-allopumiliotoxin 339 B
  参考文献：
  名称：

  The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B

  摘要：

  Short, highly stereocontrolled, asymmetric total synthesis of the title amphibian alkaloids are described. In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form. This short sequence proceeds in five laboratory operations and involves the novel intermediacy of an "unprotected" 2-acylpyrrolidine intermediate (Scheme VII). The (Z)-alkylidene side chain of the target alkaloids are introduced by stereocontrolled aldol dehydration sequences (Schemes X and XI). These enantioselective total syntheses confirm the structures and absolute configurations of the allopumiliotoxins 267A and 339B.

  DOI：

  10.1021/jo00030a026
• 作为产物：
  描述：

  (R)-α-Methyl-α-(1-methoxypropadienyl)-2(S)-pyrrolidinemethanol 在 盐酸 、 4-二甲氨基吡啶 、 sodium tetrahydroborate 、 正丁基锂 、 cerium(III) chloride 、 (三苯基甲基)-锂 、 氨 、 sodium 、 对甲苯磺酸 、 1,8-二氮杂双环[5.4.0]十一碳-7-烯 、 三乙胺 、 三氟乙酸酐 作用下， 以 四氢呋喃 、 乙醇 为溶剂， 反应 31.75h， 生成 (8R,8aS)-7-<<(Dimethylethyl)dimethylsilyl>oxy>-8-hydroxy-8-methyl-6-<(Z)-2(R)-methyl-4-hydroxybutylidene>octahydroindolizine
  参考文献：
  名称：

  The first enantioselective total syntheses of the allopumiliotoxin A alkaloids 267A and 339B

  摘要：

  Short, highly stereocontrolled, asymmetric total synthesis of the title amphibian alkaloids are described. In the first stage the indolizidine ketone 11 is assembled from L-proline in enantiomerically pure form. This short sequence proceeds in five laboratory operations and involves the novel intermediacy of an "unprotected" 2-acylpyrrolidine intermediate (Scheme VII). The (Z)-alkylidene side chain of the target alkaloids are introduced by stereocontrolled aldol dehydration sequences (Schemes X and XI). These enantioselective total syntheses confirm the structures and absolute configurations of the allopumiliotoxins 267A and 339B.

  DOI：

  10.1021/jo00030a026