(-)-ainsliadimer B | 1089724-16-2

• 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: (-)-ainsliadimer B
• 英文别名: ainsliadimer B；(1S,2S,3'aS,6S,6'aR,9R,9'aR,9'bS,12R,15R)-9-hydroxy-15-(hydroxymethyl)-3',5,6'-trimethylidenespiro[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: 1089724-16-2
• 化学式: C₃₀H₃₂O₈
• 分子量: 520.579
• InChiKey: RHYDACDYAGGAEH-BIIRDFIDSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1
• 重原子数：
  38
• 可旋转键数：
  1
• 环数：
  7.0
• sp3杂化的碳原子比例：
  0.6
• 拓扑面积：
  127
• 氢给体数：
  2
• 氢受体数：
  8

反应信息

• 作为反应物：
  描述：

  (-)-ainsliadimer B 在 N,N'-二环己基碳二亚胺 、 copper(l) chloride 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以83%的产率得到(-)-gochnatiolides B
  参考文献：
  名称：

  Ainsliadimer B和Gonnatiolide A和B的总合成

  摘要：

  噢，我的天哪：用25个步骤完成了α-桑顿酸合成ainsliadimer B和gochnatiolide A和B的总产率约为1％。天然脱氢zaluzanin C与单体愈创木酚内酯衍生物的Diels-Alder反应可以立体选择性地组装二聚体gochnatiolide型骨架，并具有所需的立体化学和用于合成二聚体insinadimer B和gochnatiolides A和B的预装功能（参见方案）。

  DOI：

  10.1002/chem.201204292
• 作为产物：
  描述：

  (-)-gochnatiolides B 在 盐酸 、 水 作用下， 以 二氯甲烷 、 丙酮 为溶剂， 反应 168.0h， 以27%的产率得到(-)-ainsliadimer B
  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

• Total Syntheses of Ainsliadimer B and Gochnatiolides A and B
  作者：Dongliang Xia、Yu Du、Zhi Yi、Hao Song、Yong Qin

  DOI：10.1002/chem.201204292

  日期：2013.4.2

  syntheses of ainsliadimer B and gochnatiolides A and B from α‐santonin have been accomplished in 25 steps with approximately 1 % overall yield. A Diels–Alder reaction of natural dehydrozaluzanin C with a monomeric guaianolide derivative allows stereoselective assembly of a dimeric gochnatiolide‐type skeleton with the required stereochemistry and preinstalled functionalities for the synthesis of dimeric

  噢，我的天哪：用25个步骤完成了α-桑顿酸合成ainsliadimer B和gochnatiolide A和B的总产率约为1％。天然脱氢zaluzanin C与单体愈创木酚内酯衍生物的Diels-Alder反应可以立体选择性地组装二聚体gochnatiolide型骨架，并具有所需的立体化学和用于合成二聚体insinadimer B和gochnatiolides A和B的预装功能（参见方案）。
• 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.