(3aS,4S,6aS,8S,9R,9aS,9bS)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one | 1132754-23-4

• 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: (3aS,4S,6aS,8S,9R,9aS,9bS)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
• CAS: 1132754-23-4
• 化学式: C₁₅H₂₀O₄
• 分子量: 264.321
• InChiKey: FHYQPZNZWJKLKK-KPAKIUNKSA-N

物化性质

• 沸点：
  478.1±45.0 °C(predicted)
• 密度：
  1.24±0.1 g/cm3(Temp: 20 °C; Press: 760 Torr)(predicted)

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  19
• 可旋转键数：
  0
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.67
• 拓扑面积：
  66.8
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aS,8S,9R,9aS,9bS)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 3.5h， 以96%的产率得到(-)-8-epigrosheimin
  参考文献：
  名称：

  Diastereoselective total synthesis of 8-epigrosheimin

  摘要：

  The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated gamma-butyrolactone ring. Our approach featured that the gamma-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative gamma-lactonization; and (3) an intramolecular aldehyde-ene cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.025
• 作为产物：
  描述：

  (3aS,4S,6aS,8S,9R,9aS,9bS)-4-hydroxy-8-(methoxymethoxy)-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one 在 4-甲基苯磺酸吡啶 作用下， 以 叔丁醇 为溶剂， 反应 1.0h， 以73%的产率得到(3aS,4S,6aS,8S,9R,9aS,9bS)-4,8-dihydroxy-9-methyl-3,6-dimethylidene-4,5,6a,7,8,9,9a,9b-octahydro-3aH-azuleno[4,5-b]furan-2-one
  参考文献：
  名称：

  Diastereoselective total synthesis of 8-epigrosheimin

  摘要：

  The first diastereoselective total synthesis of 8-epigrosheimin was accomplished relying entirely on substrate-controlled methods. 8-Epigrosheimin, isolated as an amoebicidal and antibiotic compound from Crepis virens, is a multi-chiral-centered guaianolide with a cis-hydroazulene and a trans-annulated gamma-butyrolactone ring. Our approach featured that the gamma-butyrolactone unit was formed firstly before the construction of the cycloheptane ring system. The key steps of the synthesis involved (1) a stereoselective Mukaiyama aldol addition; (2) an oxidative gamma-lactonization; and (3) an intramolecular aldehyde-ene cyclization. (C) 2008 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tetlet.2008.12.025