mytheciumone A

• 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: mytheciumone A
• 英文别名: 5-hydroxy-4,5-dimethyl-3a,4,6,6a-tetrahydro-3H-cyclopenta[b]furan-2-one
• 化学式: C₉H₁₄O₃
• 分子量: 170.208
• InChiKey: DZQCSLAJKGYOAF-UHFFFAOYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.6
• 重原子数：
  12
• 可旋转键数：
  0
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.89
• 拓扑面积：
  46.5
• 氢给体数：
  1
• 氢受体数：
  3

反应信息

• 作为产物：
  描述：

  在 sodium tetrahydroborate 、 [Ir(dF(CF₃)ppy)₂(dtbbpy)](PF₆) 、 氧气 、 caesium carbonate 作用下， 以 二氯甲烷 为溶剂， 生成 mytheciumone A
  参考文献：
  名称：

  CATALYST-CONTROLLED SITE-SELECTIVE METHYLENE C-H LACTONIZATION OF DICARBOXYLIC ACIDS

  摘要：

  Disclosed herein is the catalyst-controlled site-selective activation of β- and γ-methylene C-H bonds of free carboxylic acids which heretofore was unknown and has remained a tremendous challenge. Described herein in the enablement of such chemical reactivity with ubiquitous dicarboxylic acids which possess inert, methylene-rich backbones and dual functional groups which opened up pathways for the construction of complex molecular scaffolds for organic synthesis. Herein we show that with a pair of palladium catalysts, it is possible to perform highly site-selective monolactonization reactions with a wide range of dicarboxylic acids, generating topologically diverse and synthetically useful γ- and δ-lactones via site-selective β- or γ-methylene C-H activation. The remaining carboxyl group serves as a versatile linchpin for further synthetic applications as demonstrated by the total synthesis of two natural products, myrotheciumone A and pedi cellosine, from abundant dicarboxylic acids.

  公开号：

  WO2023220559A2