| 1390642-55-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• CAS: 1390642-55-3
• 化学式: C₃₀H₃₀O₈
• 分子量: 518.563
• InChiKey: HYSWBWHHKBOAGT-DYDJMOIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  3.59
• 重原子数：
  38.0
• 可旋转键数：
  1.0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  116.2
• 氢给体数：
  1.0
• 氢受体数：
  8.0

反应信息

• 作为反应物：
  描述：

  在 二甲基硫 作用下， 以 乙酸乙酯 为溶剂， 反应 30.0h， 以100%的产率得到(-)-gochnatiolides A
  参考文献：
  名称：

  Biomimetic Syntheses of (−)-Gochnatiolides A–C and (−)-Ainsliadimer B

  摘要：

  We report the first biomimetic syntheses of (-)-gochnatiolides A-C and (-)-ainsliadimer B based on our proposed biogenetic pathway. Our synthesis features one-pot cascade transformations including Saegusa oxidation, intermolecular Diels-Alder cycloaddition, and radical-mediated allylic oxidation, which allow for the rapid generation of (-)-gochnatiolides A-C in a collective manner. We also disclose an unprecedented "copper effect" on the stereochemical outcome of the radical-mediated allylic oxidation. Our synthetic endeavors led to the structural reassignment of (-)-gochnatiolide B. Ultimately, a biomimetic transformation from gochnatiolide B to ainsliadimer B was achieved through a remarkable direct enone hydration.

  DOI：

  10.1021/ja305464s
• 作为产物：
  描述：

  dehydrozaluzanin C 在 palladium diacetate 、 六甲基二硅氮烷 作用下， 以 二氯甲烷 、 二甲基亚砜 为溶剂， 反应 24.41h， 生成
  参考文献：
  名称：

  Biomimetic Syntheses of (−)-Gochnatiolides A–C and (−)-Ainsliadimer B

  摘要：

  We report the first biomimetic syntheses of (-)-gochnatiolides A-C and (-)-ainsliadimer B based on our proposed biogenetic pathway. Our synthesis features one-pot cascade transformations including Saegusa oxidation, intermolecular Diels-Alder cycloaddition, and radical-mediated allylic oxidation, which allow for the rapid generation of (-)-gochnatiolides A-C in a collective manner. We also disclose an unprecedented "copper effect" on the stereochemical outcome of the radical-mediated allylic oxidation. Our synthetic endeavors led to the structural reassignment of (-)-gochnatiolide B. Ultimately, a biomimetic transformation from gochnatiolide B to ainsliadimer B was achieved through a remarkable direct enone hydration.

  DOI：

  10.1021/ja305464s