(+/-)-yezo’otogirin C

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: (+/-)-yezo’otogirin C
• 英文别名: (±)-yezo’otogirin C；yezootogirin C；2-methyl-1-[(4R,7R,8S,11S)-3,3,7,10-tetramethyl-8-(3-methylbut-2-enyl)-2-oxatricyclo[5.3.1.04,11]undec-1(10)-en-11-yl]propan-1-one
• 化学式: C₂₃H₃₆O₂
• 分子量: 344.538
• InChiKey: DBACOFREEYSTTM-ZRGHVXQMSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.4
• 重原子数：
  25
• 可旋转键数：
  4
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.78
• 拓扑面积：
  26.3
• 氢给体数：
  0
• 氢受体数：
  2

反应信息

• 作为反应物：
  描述：

  (+/-)-yezo’otogirin C 在 间氯过氧苯甲酸 、 三氟乙酸 作用下， 以 二氯甲烷 为溶剂， 反应 1.58h， 以25%的产率得到hypermogin D
  参考文献：
  名称：

  非经典 PPAP 天然产物 yezo'otogirin C 和 hypermogin D 的仿生合成，以及 norascyronone A 的合成研究

  摘要：

  多环聚异戊二烯化酰基间苯三酚 (PPAP) 的氧化降解和重排创造了多种独特的天然产物家族，这些天然产物是仿生合成的有吸引力的目标。在此，我们报告了金丝桃素 A 的外消旋合成及其氧化自由基环化生成 yezo'otogirin C，然后进行环氧化和 House-Meinwald 重排生成 Hypermogin D。我们还研究了通过类似的自由基环化途径仿生合成 norascyronone A ，具有意想不到的结果，有助于深入了解其生物合成。

  DOI：

  10.1039/d2ob00074a
• 作为产物：
  描述：

  3-异丁氧基-2-环己烯酮 在 正丁基锂 、 碘 、 manganese (II) acetate tetrahydrate 、 manganese(III) triacetate dihydrate 、 碳酸氢钠 、 戴斯-马丁氧化剂 、 magnesium 、 二异丙胺 、 硫脲 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 甲醇 、 二氯甲烷 为溶剂， 反应 14.83h， 生成 (+/-)-yezo’otogirin C
  参考文献：
  名称：

  Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues

  摘要：

  A systematic study of the biomimetic pathways to yezo'otogirin C under aerobic and anaerobic conditions has been investigated, and both are found to be feasible pathways to the natural product depending on the physiological conditions. Because of the lower activation energy, the aerobic process would be more favorable when the in vivo oxygen level is high. In the course of this study, a highly efficient synthetic route to (+/-)-yezo'otogirin C has been established in four steps (31% overall yield) from a readily available compound without using any protecting groups. The natural product and its structural analogues exhibited antitumor activities against several human cancer cell lines and appeared to arrest cell cycles in different phases.

  DOI：

  10.1021/jo502267g

文献信息

• Bioinspired Total Synthesis of (±)-Yezo’otogirin C
  作者：Shuzhong He、Wei Yang、Lizhi Zhu、Guangyan Du、Chi-Sing Lee

  DOI：10.1021/ol403374h

  日期：2014.1.17

  The first and protective group-free total synthesis of (+/-)-yezo'otogirin C has been achieved from 3-methyl-4-prenylcyclohex-2-enone in eight steps with 23% overall yield. The tricyclic core of (+/-)-yezo'otogirin C was established via a bioinspired oxidative cascade cyclization strategy using Mn(II)/Mn(III) and O-2, followed by reduction of the peroxy-bridged intermediate using thiourea in refluxing methanol.
• Systemic Study on the Biogenic Pathways of Yezo’otogirins: Total Synthesis and Antitumor Activities of (±)-Yezo’otogirin C and Its Structural Analogues
  作者：Wei Yang、Jingming Cao、Mengxun Zhang、Rongfeng Lan、Lizhi Zhu、Guangyan Du、Shuzhong He、Chi-Sing Lee

  DOI：10.1021/jo502267g

  日期：2015.1.16

  A systematic study of the biomimetic pathways to yezo'otogirin C under aerobic and anaerobic conditions has been investigated, and both are found to be feasible pathways to the natural product depending on the physiological conditions. Because of the lower activation energy, the aerobic process would be more favorable when the in vivo oxygen level is high. In the course of this study, a highly efficient synthetic route to (+/-)-yezo'otogirin C has been established in four steps (31% overall yield) from a readily available compound without using any protecting groups. The natural product and its structural analogues exhibited antitumor activities against several human cancer cell lines and appeared to arrest cell cycles in different phases.
• Biomimetic synthesis of the non-canonical PPAP natural products yezo'otogirin C and hypermogin D, and studies towards the synthesis of norascyronone A
  作者：Stefania A. Sassnink、Quang D. Phan、Hiu C. Lam、Aaron J. Day、Lauren A. M. Murray、Jonathan H. George

  DOI：10.1039/d2ob00074a

  日期：——

  (PPAPs) has created diverse families of unique natural products that are attractive targets for biomimetic synthesis. Herein, we report a racemic synthesis of hyperibrin A and its oxidative radical cyclization to give yezo'otogirin C, followed by epoxidation and House–Meinwald rearrangement to give hypermogin D. We also investigated the biomimetic synthesis of norascyronone A via a similar radical cyclization

  多环聚异戊二烯化酰基间苯三酚 (PPAP) 的氧化降解和重排创造了多种独特的天然产物家族，这些天然产物是仿生合成的有吸引力的目标。在此，我们报告了金丝桃素 A 的外消旋合成及其氧化自由基环化生成 yezo'otogirin C，然后进行环氧化和 House-Meinwald 重排生成 Hypermogin D。我们还研究了通过类似的自由基环化途径仿生合成 norascyronone A ，具有意想不到的结果，有助于深入了解其生物合成。