(1S,4Z,13S,14S)-8,11-dimethoxy-5-methyl-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7,9,11-tetraen-16-one | 916601-53-1

• 分子结构分类: 有机化合物 - 苯类化合物 - 苯酚醚
• 英文名称: (1S,4Z,13S,14S)-8,11-dimethoxy-5-methyl-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7,9,11-tetraen-16-one
• CAS: 916601-53-1
• 化学式: C₁₈H₂₀O₅
• 分子量: 316.354
• InChiKey: XMKSCHPCHLHZRU-IWIWSICTSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.3
• 重原子数：
  23
• 可旋转键数：
  2
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.5
• 拓扑面积：
  57.3
• 氢给体数：
  0
• 氢受体数：
  5

反应信息

• 作为反应物：
  描述：

  (1S,4Z,13S,14S)-8,11-dimethoxy-5-methyl-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7,9,11-tetraen-16-one 在 ammonium cerium(IV) nitrate 作用下， 以 水 、 乙腈 为溶剂， 反应 0.17h， 以69%的产率得到clavilactone B
  参考文献：
  名称：

  Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of ent-Clavilactone B

  摘要：

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.

  DOI：

  10.1021/ja0662671
• 作为产物：
  描述：

  (S)-[(2S,3R)-3-but-3-enyl-3-[[tert-butyl(diphenyl)silyl]oxymethyl]oxiran-2-yl]-[3,6-dimethoxy-2-(2-methylprop-2-enyl)phenyl]methanol 在 RuCl2(1,3-dimesityl-imidazolidin-2-yl)(PCy3)(=CHPh) 2,2,6,6-tetramethyl-piperidine-N-oxyl 、 四氟对苯醌 、 碘苯二乙酸 、 四丁基氟化铵 作用下， 以 四氢呋喃 、 二氯甲烷 、 甲苯 为溶剂， 反应 39.0h， 生成 (1S,4Z,13S,14S)-8,11-dimethoxy-5-methyl-15,17-dioxatetracyclo[11.2.2.01,14.07,12]heptadeca-4,7,9,11-tetraen-16-one
  参考文献：
  名称：

  Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of ent-Clavilactone B

  摘要：

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.

  DOI：

  10.1021/ja0662671

文献信息

• Highly Convergent Three Component Benzyne Coupling:  The Total Synthesis of <i>ent</i>-Clavilactone B
  作者：Igor Larrosa、Marianne I. Da Silva、Patricio M. Gómez、Peter Hannen、Eunjung Ko、Steven R. Lenger、Simon R. Linke、Andrew J. P. White、Donna Wilton、Anthony G. M. Barrett

  DOI：10.1021/ja0662671

  日期：2006.11.1

  The first total synthesis of (+)-clavilactone B, a potent antifungal agent and novel tyrosine kinase inhibitor, is described. The absolute configuration of clavilactones has been unambiguously established by using Sharpless asymmetric epoxidation to generate the enantiomerically pure substrate. The strategy highlights the use of a powerful and convergent three-component benzyne coupling with a methylallyl Grignard and a chiral epoxy-aldehyde to generate two C-C bonds and install the carbon skeleton of clavilactone. Oxidative lactonization, ten-membered ring construction by ring closing metathesis, and oxidation gave clavilactone B.