(-)-gochnatiolide C | 103701-75-3

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: (-)-gochnatiolide C
• 英文别名: gochnatiolide C；gochnatiolid C；(1R,2S,3'aS,6S,6'aR,9R,9'aR,9'bS,12R)-3',5,6',15-tetramethylidenespiro[3-oxatetracyclo[7.6.1.02,6.013,16]hexadec-13(16)-ene-12,9'-4,5,6a,7,9a,9b-hexahydro-3aH-azuleno[4,5-b]furan]-2',4,8',14-tetrone
• CAS: 103701-75-3
• 化学式: C₃₀H₃₀O₆
• 分子量: 486.565
• InChiKey: ZTOZCSMGEIDJAP-HBQGZYEKSA-N

物化性质

• 熔点：
  119-121 °C
• 沸点：
  763.8±60.0 °C(Predicted)
• 密度：
  1.32±0.1 g/cm3(Predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  3.1
• 重原子数：
  36
• 可旋转键数：
  0
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.53
• 拓扑面积：
  86.7
• 氢给体数：
  0
• 氢受体数：
  6

反应信息

• 作为反应物：
  描述：

  (-)-gochnatiolide C 在 potassium fluoride 、 氧气 作用下， 以 二甲基亚砜 为溶剂， 反应 60.0h， 以23%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 0.41h， 生成 (-)-gochnatiolide C
  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

文献信息

• Biomimetic Syntheses of (−)-Gochnatiolides A–C and (−)-Ainsliadimer B
  作者：Chao Li、Longyang Dian、Weidong Zhang、Xiaoguang Lei

  DOI：10.1021/ja305464s

  日期：2012.8.1

  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.