(2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-pent-4-enyl-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester | 171523-50-5

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-pent-4-enyl-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
• 英文别名: 1-O-benzyl 2-O-methyl (2S,3aR,4S,7R,7aR)-4-[2-(dimethylamino)-2-oxoethyl]-7-pent-4-enyl-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylate
• CAS: 171523-50-5
• 化学式: C₂₇H₃₆N₂O₅
• 分子量: 468.593
• InChiKey: SYLHWUGLIVDTJC-COWNTTACSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.2
• 重原子数：
  34
• 可旋转键数：
  11
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.52
• 拓扑面积：
  76.2
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-pent-4-enyl-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 palladium dihydroxide 劳森试剂 、 咪唑 、 六甲基磷酰三胺 、 4-二甲氨基吡啶 、 lithium hydroxide 、 sodium chlorite 、 sodium tetrahydroborate 、 sodium periodate 、 四氧化锇 、 phosphate buffer 、 偶氮二异丁腈 、 三丁基膦 、 五氟苯基二苯基磷酸酯 、 氢氟酸 、 氢气 、 双氧水 、 碘 、 三正丁基氢锡 、 戴斯-马丁氧化剂 、 二氯磷酸苯酯 、 氢化奎尼定 1,4-(2,3-二氮杂萘)二醚 、 三乙胺 、 sodium phosphate 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 水 、 乙腈 、 xylene 为溶剂， 反应 141.25h， 生成 (-)-4-thiostenine
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine

  摘要：

  Stenine can be extracted from the roots of the Chinese medicinal plant Stemona tuberosa (Stemonaceae), and its structure and absolute configuration were derived by comparison to the major Stemona alkaloid tuberostemonine. We report the first enantioselective total synthesis of (-)-stenine by a strategy that takes advantage of a diastereoselective end-group-differentiating cyclization in the oxidation of L-tyrosine, The resulting cis-fused indolone is converted to the trans-fused core of stenine upon reduction of a pi-allylpalladium complex, and by stereoselective introduction of four additional stereocenters, a butyrolactone and an azepine ring are attached to this alkaloid building block.

  DOI：

  10.1021/ja00150a010
• 作为产物：
  描述：

  (2S,3aR,7aR)-3a-hydroxy-6-oxo-2,3,3a,6,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester 在 吡啶 、 4-二甲氨基吡啶 、 tris(dibenzylideneacetone)dipalladium(0) chloroform complex 、 sodium tetrahydroborate 、 甲酸 、 cerium(III) chloride 、 四丙基高钌酸铵 、 potassium hexamethyldisilazane 、 三丁基膦 、 N-甲基吗啉氧化物 、 三乙胺 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 、 异丙醚 、 xylene 为溶剂， 反应 65.5h， 生成 (2S,3aR,4S,7R,7aS)-4-((dimethylcarbamoyl)methyl)-7-pent-4-enyl-2,3,3a,4,7,7a-hexahydroindole-1,2-dicarboxylic acid 1-benzyl ester 2-methyl ester
  参考文献：
  名称：

  Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine

  摘要：

  Stenine can be extracted from the roots of the Chinese medicinal plant Stemona tuberosa (Stemonaceae), and its structure and absolute configuration were derived by comparison to the major Stemona alkaloid tuberostemonine. We report the first enantioselective total synthesis of (-)-stenine by a strategy that takes advantage of a diastereoselective end-group-differentiating cyclization in the oxidation of L-tyrosine, The resulting cis-fused indolone is converted to the trans-fused core of stenine upon reduction of a pi-allylpalladium complex, and by stereoselective introduction of four additional stereocenters, a butyrolactone and an azepine ring are attached to this alkaloid building block.

  DOI：

  10.1021/ja00150a010

文献信息

• Asymmetric Total Synthesis of the Stemona Alkaloid (-)-Stenine
  作者：Peter Wipf、Yuntae Kim、David M. Goldstein

  DOI：10.1021/ja00150a010

  日期：1995.11

  Stenine can be extracted from the roots of the Chinese medicinal plant Stemona tuberosa (Stemonaceae), and its structure and absolute configuration were derived by comparison to the major Stemona alkaloid tuberostemonine. We report the first enantioselective total synthesis of (-)-stenine by a strategy that takes advantage of a diastereoselective end-group-differentiating cyclization in the oxidation of L-tyrosine, The resulting cis-fused indolone is converted to the trans-fused core of stenine upon reduction of a pi-allylpalladium complex, and by stereoselective introduction of four additional stereocenters, a butyrolactone and an azepine ring are attached to this alkaloid building block.