(2R,4R,6S,9R,10S)-16-(benzenesulfonyl)-9,10-dimethyl-5-oxa-16-azahexacyclo[11.11.0.02,6.02,10.015,23.017,22]tetracosa-1(24),13,15(23),17,19,21-hexaen-4-ol | 1374409-94-5

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吲哚及其衍生物
• 英文名称: (2R,4R,6S,9R,10S)-16-(benzenesulfonyl)-9,10-dimethyl-5-oxa-16-azahexacyclo[11.11.0.02,6.02,10.015,23.017,22]tetracosa-1(24),13,15(23),17,19,21-hexaen-4-ol
• CAS: 1374409-94-5
• 化学式: C₃₀H₃₁NO₄S
• 分子量: 501.646
• InChiKey: JECPHRMZFURKKY-JEGXWDCPSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.7
• 重原子数：
  36
• 可旋转键数：
  2
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.4
• 拓扑面积：
  76.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (2R,4R,6S,9R,10S)-16-(benzenesulfonyl)-9,10-dimethyl-5-oxa-16-azahexacyclo[11.11.0.02,6.02,10.015,23.017,22]tetracosa-1(24),13,15(23),17,19,21-hexaen-4-ol 在 4-二甲氨基吡啶 、 四(三苯基膦)钯 、 Hoveyda-Grubbs catalyst second generation 、 甲酸铵 、 二异丁基氢化铝 、 三乙胺 作用下， 以 四氢呋喃 、 hexanes 、 二氯甲烷 、 甲苯 为溶剂， 反应 1.17h， 生成 N-benzenesulfonyl-tubingensin A
  参考文献：
  名称：

  Total Syntheses of Anominine and Tubingensin A

  摘要：

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

  DOI：

  10.1021/ja302765m
• 作为产物：
  描述：

  (2R,4R,6S,9R,10S)-16-(benzenesulfonyl)-4-ethoxy-9,10-dimethyl-5-oxa-16-azahexacyclo[11.11.0.02,6.02,10.015,23.017,22]tetracosa-1(24),13,15(23),17,19,21-hexaene 在 高氯酸 作用下， 以 四氢呋喃 、 水 为溶剂， 反应 4.0h， 以94%的产率得到(2R,4R,6S,9R,10S)-16-(benzenesulfonyl)-9,10-dimethyl-5-oxa-16-azahexacyclo[11.11.0.02,6.02,10.015,23.017,22]tetracosa-1(24),13,15(23),17,19,21-hexaen-4-ol
  参考文献：
  名称：

  Total Syntheses of Anominine and Tubingensin A

  摘要：

  A divergent strategy for the total syntheses of the indole terpenoid anominine (1) and its natural congener tubingensin A (2) has been developed. The common intermediate 11 bearing all of the required stereogenic centers for both natural products was first assembled by employing a Ueno-Stork radical cyclization and a Sc(OTf)(3)-mediated Mukaiyama aldol reaction to form the key C-C bonds in a stereocontrolled manner. The route to anominine features a radical deoxygenation followed by an efficient side-chain installation, while the path to tubingensin A exploits a CuOTf-promoted 6 pi-electrocyclization/aromatization sequence to forge the central region of the pentacyclic scaffold.

  DOI：

  10.1021/ja302765m