connatusin B | 871331-94-1

• 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: connatusin B
• 英文别名: (3S,3aS,3bR,4R,6aS)-3,4-dihydroxy-3-(hydroxymethyl)-3a,5,5-trimethyl-4,6,6a,7-tetrahydro-3bH-cyclopenta[a]pentalen-2-one
• CAS: 871331-94-1
• 化学式: C₁₅H₂₂O₄
• 分子量: 266.337
• InChiKey: BWDRVAKXNVFADI-VOUTZNEASA-N

计算性质

• 辛醇/水分配系数(LogP)：
  0.8
• 重原子数：
  19
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.8
• 拓扑面积：
  77.8
• 氢给体数：
  3
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  [(3'aS,3'bR,4S,4'R,6'aS)-2,2,3'a,5',5'-pentamethyl-2'-oxospiro[1,3-dioxolane-4,3'-4,6,6a,7-tetrahydro-3bH-cyclopenta[a]pentalene]-4'-yl] acetate 在 水 作用下， 以 甲醇 为溶剂， 反应 16.0h， 以77%的产率得到connatusin B
  参考文献：
  名称：

  A chemoenzymatic total synthesis of the hirsutene-type sesquiterpene (+)-connatusin B from toluene

  摘要：

  The first total synthesis of the hirsutene-type sesquiterpenoid natural product (+)-connatusin B (2) is reported. The cis-1,2-dihydrocatechol 3, which is obtained in enantiomerically pure form via the enzymatic dihydroxylation of toluene, served as the starting material. Diels-Alder cycloaddition and oxa-di-pi-methane rearrangement reactions represent key chemical steps in the reaction sequence leading to the cyclopropane ring-fused linear triquinane 14. Reductive cleavage of the three-membered ring within this framework and various functional group interconversions then provide the title compound 2. (C) 2010 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2010.07.059