(3aS,4S,6aS,8S,9R,9aS,9bS)-4-hydroxy-8-(methoxymethoxy)-9-methyl-6-methylidene-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2-one | 1132754-21-2

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 内酯类
• 英文名称: (3aS,4S,6aS,8S,9R,9aS,9bS)-4-hydroxy-8-(methoxymethoxy)-9-methyl-6-methylidene-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2-one
• CAS: 1132754-21-2
• 化学式: C₁₆H₂₄O₅
• 分子量: 296.364
• InChiKey: YHFICQPYNPNFCC-CYLOYZKTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.1
• 重原子数：
  21
• 可旋转键数：
  3
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.81
• 拓扑面积：
  65
• 氢给体数：
  1
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (3aS,4S,6aS,8S,9R,9aS,9bS)-4-hydroxy-8-(methoxymethoxy)-9-methyl-6-methylidene-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[4,5-b]furan-2-one 、 n,n-二甲基亚甲基碘化胺 在 lithium diisopropyl amide 、 间氯过氧苯甲酸 作用下， 以 四氢呋喃 、 氯仿 为溶剂， 反应 1.0h， 以72%的产率得到(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
  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：

  (2S,3R)-2-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]-5-oxooxolane-3-carbaldehyde 在 二异丙氧基二氯化钛 作用下， 以 二氯甲烷 为溶剂， 反应 5.0h， 以1.604 g的产率得到(3aS,4S,6aS,8S,9R,9aS,9bS)-4-hydroxy-8-(methoxymethoxy)-9-methyl-6-methylidene-3,3a,4,5,6a,7,8,9,9a,9b-decahydroazuleno[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