(1S*,7R*,8aS*)-1,7-dihydroxyindolizidine | 145388-59-6

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡咯里西啶类
• 英文名称: (1S*,7R*,8aS*)-1,7-dihydroxyindolizidine
• 英文别名: 1,7-dihydroxyindolizidine；(1R,7S,8aR)-1,2,3,5,6,7,8,8a-octahydroindolizine-1,7-diol
• CAS: 145388-59-6
• 化学式: C₈H₁₅NO₂
• 分子量: 157.213
• InChiKey: SWCWEPTZLZWDFJ-XLPZGREQSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  -0.3
• 重原子数：
  11
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  43.7
• 氢给体数：
  2
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  (1S*,7R*,8aS*)-1-[(tert-butyldimethylsilyl)oxy]-7-hydroxyindolizidine 在 盐酸 作用下， 反应 10.0h， 以99%的产率得到(1S*,7R*,8aS*)-1,7-dihydroxyindolizidine
  参考文献：
  名称：

  Stereoselective Synthesis of Polyhydroxylated Indolizidines from γ-Hydroxy α,β-Unsaturated Sulfones

  摘要：

  The polyhydroxylated indolizidines castanospermine and swainsonine as well as some of their stereoisomers are powerful glycosidase inhibitors. An efficient and stereochemically flexible synthesis of racemic 1,7,8-trihydroxylated and 1,6,7,8-tetrahydroxylated indolizidines (castanospermine stereoisomers) from readily available N-substituted gamma-oxygenated alpha,beta-unsaturated sulfones 3 and 4 has been developed. The construction of the bicyclic skeleton of 1-hydroxyindolizidine has been accomplished by intramolecular conjugate addition of the nitrogen moiety of 3 and 4 to the alpha,beta-unsaturated sulfone unit to give the pyrrolidine intermediates 5 and 6, followed by formation of the C(7)-C(8) bond by intramolecular acylation (or alkylation) of the alpha-sulfonyl carbanion. The stereoselectivity of the pyrrolidine synthesis was highly dependent on the bulkiness of the gamma-oxygenated function; thus, the free alcohols gave predominantly cis-pyrrolidines while the OTIPS derivatives led to the trans isomers. After straightforward functional group transformations, the removal of the sulfonyl group at C(8) either by Julia reaction or by basic elimination (depending on the substrate used) afforded the key C(7)C(8) unsaturated indolizidines 10, 22, 30, and 31, whose stereoselective dihydroxylations with OsO4 gave a variety of cis C(1)C(8a) and-trans C(1)C(8a) trihydroxylated and tetrahydroxylated indolizidines, among which (+/-)-1,7-di-epi-castanospermine and (+/-)-1,8-di-epi-castanospermine have been reported for the first time.

  DOI：

  10.1021/jo972167p

文献信息

• Synthesis of (−)-8-deoxy-7-hydroxy-swainsonine and (±)-6,8-dideoxy-castanospermine
  作者：Michele Maggini、Maurizio Prato、Massimo Ranelli、Gianfranco Scorrano

  DOI：10.1016/s0040-4039(00)79036-8

  日期：1992.10

  A total synthesis of (1S,2R,7S,8aR)-1,2,7-trihydroxyindolizidine 3 has been achieved in few steps from lactam 4. The dihydroxyderivative 14 has also been PrePared with the same general synthetic approach adapting a Michael addition and a thioamide-diazoketone cyclocondensation as key steps.