(2R,3a'S,5'R)-5'-pentyl-3'3a',4,5,5',6'-hexahydro-3H-spiro[furan-2,2'pyrano[2,3,4-de]chromen]-8'-ol | 1223536-17-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 苯并吡喃
• 英文名称: (2R,3a'S,5'R)-5'-pentyl-3'3a',4,5,5',6'-hexahydro-3H-spiro[furan-2,2'pyrano[2,3,4-de]chromen]-8'-ol
• 英文别名: (3R,5S,7R)-7-pentylspiro[2,6-dioxatricyclo[7.3.1.05,13]trideca-1(12),9(13),10-triene-3,2'-oxolane]-11-ol
• CAS: 1223536-17-1
• 化学式: C₁₉H₂₆O₄
• 分子量: 318.413
• InChiKey: KFQMOEAYRBBNLG-HHXXYDBFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.1
• 重原子数：
  23
• 可旋转键数：
  4
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.68
• 拓扑面积：
  47.9
• 氢给体数：
  1
• 氢受体数：
  4

反应信息

• 作为产物：
  描述：

  1-[(3R)-3-pentyl-6,8-bis(phenylmethoxy)-3,4-dihydro-1H-isochromen-1-yl]-5-phenylmethoxypentan-2-one 在 盐酸 、 氢气 、 palladium(II) hydroxide 作用下， 反应 18.0h， 生成 (2R,3a'S,5'R)-5'-pentyl-3'3a',4,5,5',6'-hexahydro-3H-spiro[furan-2,2'pyrano[2,3,4-de]chromen]-8'-ol 、
  参考文献：
  名称：

  An Enantioselective Formal Synthesis of Berkelic Acid

  摘要：

  An enantioselective formal synthesis of berkelic acid is described. The key step Involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.

  DOI：

  10.1021/ol202265g

文献信息

• A flexible asymmetric synthesis of the tetracyclic core of berkelic acid using a Horner–Wadsworth–Emmons/oxa-Michael cascade
  作者：Zoe E. Wilson、Margaret A. Brimble

  DOI：10.1039/b927219b

  日期：——

  The one-pot Horner–Wadsworth–Emmons/oxa-Michael cascade followed by spiroketalisation affords the tetracyclic benzannulated spiroketal core of berkelic acid, an extremophile natural product with selective activity against ovarian cancer.

  一锅法的霍纳-瓦兹沃斯-埃门斯/氧桥-迈克尔级联反应 followed by spiroketal化反应，得到四环芳香化的螺旋酮核心，即伯克利酸，这是一种对卵巢癌具有选择性活性的极端嗜好者天然产物。
• An Enantioselective Formal Synthesis of Berkelic Acid
  作者：Michael C. McLeod、Zoe E. Wilson、Margaret A. Brimble

  DOI：10.1021/ol202265g

  日期：2011.10.7

  An enantioselective formal synthesis of berkelic acid is described. The key step Involves a late-stage silyl enol ether addition to a benzannulated oxonium ion with subsequent spiroketalization leading to construction of the tetracyclic core. Thermodynamically controlled equilibration under acidic conditions affords the desired spiroketal configuration as a single diastereoisomer.