(1S,2R,8aR)-(-)-1,2-di-O-isopropylidenindolizidine | 108866-46-2

• 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: (1S,2R,8aR)-(-)-1,2-di-O-isopropylidenindolizidine
• 英文别名: (3aR,9aR,9bS)-2,2-dimethyl-3a,4,6,7,8,9,9a,9b-octahydro-[1,3]dioxolo[4,5-a]indolizine
• CAS: 108866-46-2
• 化学式: C₁₁H₁₉NO₂
• 分子量: 197.277
• InChiKey: XWNVDPBHLHETAF-BBBLOLIVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.37
• 重原子数：
  14.0
• 可旋转键数：
  0.0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  1.0
• 拓扑面积：
  21.7
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为反应物：
  描述：

  (1S,2R,8aR)-(-)-1,2-di-O-isopropylidenindolizidine 在 盐酸 作用下， 反应 6.0h， 生成 (1S,2R,8aR)-1,2-dihydroxy-octahydro-1H-indolizinium chloride
  参考文献：
  名称：

  (1S,2R,8aS)-1,2-Dihydroxyindolizidine formation by Rhizoctonia leguminicola, the fungus that produces slaframine and swainsonine

  摘要：

  DOI：

  10.1021/jo00390a024
• 作为产物：
  描述：

  (2R,3S,4R)-(-)-N-vinylacetyl-3,4-di-O-isopropylidene-2-vinylpyrrolidine 在 10percent Pd on carbon Grubbs catalyst first generation 、 dimethyl sulfide borane 、 氢气 作用下， 以 四氢呋喃 、 甲醇 、 苯 为溶剂， 反应 3.0h， 生成 (1S,2R,8aR)-(-)-1,2-di-O-isopropylidenindolizidine
  参考文献：
  名称：

  Stereoisomeric Sugar-Derived Indolizines as Versatile Building Blocks:  Synthesis of Enantiopure Di- and Tetrahydroxyindolizidines

  摘要：

  The synthesis of the sugar-derived (1S,2R,8aR)-1,2-di-O-isopropylidene-1,2,3,5,6,8a-hexahydro-5- oxoindolizine (8) and by analogy of the corresponding stereoisomers ent-8 and ent-7, an epimer at C-2 of ent-8, has been accomplished in a straightforward manner. The carbon-carbon double bond and the carbonyl functionalities on the six-membered ring make these nitrogen-containing heterocycles useful building blocks for the efficient preparation of a variety of enantiopure polyhydroxylated indolizidines of interest for their glycosidase inhibitory activity. We report here the synthesis of 2,8a-diepilentiginosine 12 from 8 and the preparation of stereoisomeric 1,2,7,8-tetrahydroxyindolizidines 9-11 performed by OsO4-catalyzed double bond syn dihydroxylation of 7 and 8, followed by deoxygenation of the amide group.

  DOI：

  10.1021/jo0016428

文献信息

• Concise and divergent total synthesis of swainsonine, 7-alkyl swainsonines, and 2,8a-diepilentiginosine via a chiral heterocyclic enaminoester intermediate
  作者：Gao-Feng Shi、Jia-Qi Li、Xiao-Ping Jiang、Ying Cheng

  DOI：10.1016/j.tet.2008.03.080

  日期：2008.5

  The concise and divergent total syntheses of (−)-swainsonine, (−)-7-alkyl swainsonines, and (−)-2,8a-diepilentiginosine from a common chiral heterocyclic enaminoester intermediate in five-step sequences are presented. The highly efficient annulation reaction of the chiral heterocyclic enaminoester with various α,β-unsaturated carboxylates, and a straightforward carboxy inversion constituted the key

  从五个步骤序列中，从一个常见的手性杂环烯胺酯中间体中得出了（-）-swainsonine，（-）-7-烷基swainsonines和（-）-2,8a-dipilentiginosine的简明和不同的总合成物。手性杂环烯胺酸酯与各种α，β-不饱和羧酸酯的高效环合反应以及直接的羧基转化是合成途径的关键特征。这项工作为从容易获得的平台不同合成不同的天然和非天然多羟基吲哚并吡啶类化合物提供了一个实例。
• The intramolecular cycloaddition of azides with ω-chloroalkenes. A facile route to (±)-swainsonine and other indolizidine alkaloids
  作者：William H. Pearson、Ko-Chung Lin

  DOI：10.1016/s0040-4039(00)97301-5

  日期：1990.1

  A potentially general route to the 1-azabicyclo[n.m.O]alkane skeleton of various alkaloids is embodied in the intramolecular 1,3-dipolar cycloaddition of aliphatic azides with ω-chloroalkenes. Cycloaddition is followed by rearrangement and intramolecular N-alkylation, affording bicyclic iminium ions1 in one operation. The application of this method to the synthesis of (±)-δ-coniceine6, (1S,2R,8aR)-indolizidine-1

  脂肪族叠氮化物与ω-氯烯烃的分子内1,3-偶极环加成反应了通往各种生物碱的1-氮杂双环[nmO]烷烃骨架的潜在一般路线。环加成后进行重排和分子内N-烷基化，一次操作即可得到双环亚胺鎓离子1。描述了该方法在合成（±）-δ-可卡因6，（1S，2R，8aR）-吲哚并吡啶-1，2-二醇13和（-）-芥子碱15中的应用。
• Biosynthesis of the toxic indolizidine alkaloids slaframine and swainsonine in Rhizoctonia leguminicola: metabolism of 1-hydroxyindolizidines
  作者：Constance M. Harris、Marilyn J. Schneider、Frank S. Ungemach、James E. Hill、Thomas M. Harris

  DOI：10.1021/ja00211a039

  日期：1988.2.3
• PEARSON, WILLIAM H.;LIN, KO-CHUNG, TETRAHEDRON LETT., 31,(1990) N2, C. 7571-7574
  作者：PEARSON, WILLIAM H.、LIN, KO-CHUNG

  DOI：——

  日期：——