(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde | 1132754-11-0

• 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: (1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde
• CAS: 1132754-11-0
• 化学式: C₁₂H₂₀O₃
• 分子量: 212.289
• InChiKey: ZZRXWCZIMHFGKV-KKOKHZNYSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2
• 重原子数：
  15
• 可旋转键数：
  5
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  35.5
• 氢给体数：
  0
• 氢受体数：
  3

反应信息

• 作为反应物：
  描述：

  γ-丁内酯 、 (1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde 在 zinc(II) chloride 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 为溶剂， 反应 2.5h， 以87%的产率得到(3S)-3-[(S)-hydroxy-[(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentyl]methyl]oxolan-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：

  C₁₂H₂₂O₃ 在 2-碘酰基苯甲酸 作用下， 以 二甲基亚砜 为溶剂， 反应 0.58h， 以98%的产率得到(1S,2R,3S,5S)-3-(methoxymethoxy)-2-methyl-5-prop-1-en-2-ylcyclopentane-1-carbaldehyde
  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

文献信息

• Diastereoselective total synthesis of 8-epigrosheimin
  作者：Haishen Yang、Xiaoxiao Qiao、Fangyi Li、Hui Ma、Longguan Xie、Xiaohua Xu

  DOI：10.1016/j.tetlet.2008.12.025

  日期：2009.3

  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.