cyercene A

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 吡喃
• 英文名称: cyercene A
• 化学式: C₁₆H₂₂O₃
• 分子量: 262.349
• InChiKey: LPDSVBCPAZAWDN-AHPWUWHXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  4.02
• 重原子数：
  19.0
• 可旋转键数：
  4.0
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.44
• 拓扑面积：
  39.44
• 氢给体数：
  0.0
• 氢受体数：
  3.0

反应信息

• 作为产物：
  描述：

  4-甲基庚烷-3,5-二酮 在 lithium carbonate 、 sodium hydride 、 三乙胺 、 lithium hexamethyldisilazane 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 、 N,N-二甲基甲酰胺 、 丙酮 为溶剂， 反应 92.34h， 生成 cyercene A
  参考文献：
  名称：

  Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A

  摘要：

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.

  DOI：

  10.1016/j.tet.2007.03.057

文献信息

• An efficient synthesis of cyercene A
  作者：John E. Moses、Jack E. Baldwin、Robert M. Adlington

  DOI：10.1016/j.tetlet.2004.06.125

  日期：2004.8

  An efficient approach to the total synthesis of the marine derived polypropionate cyercene A is described. A key feature of the synthesis is the development of methodology for the diastereoselective Wadsworth-Emmons type condensation of a functionalised gamma-pyrone unit. (C) 2004 Elsevier Ltd. All rights reserved.
• Total synthesis of cyercene A and the biomimetic synthesis of (±)-9,10-deoxytridachione and (±)-ocellapyrone A
  作者：Raphaël Rodriguez、Robert M. Adlington、Serena J. Eade、Magnus W. Walter、Jack E. Baldwin、John E. Moses

  DOI：10.1016/j.tet.2007.03.057

  日期：2007.5

  This paper summarises our detailed study towards the biomimetic synthesis of the complex polypropionate derived natural product (+/-)-9,10-deoxytridachione. A previous study based on the elaboration of functionalised gamma-pyrones allowed us to synthesise cyercene A. The same efficient methodology has been applied for the elaboration of a more complex fully conjugated gamma-pyrone polyene. Our approach centred on a key tandem Suzuki-coupling/electrocyclisation reaction, which supports a possible biosynthetic pathway for this class of natural products. A related compound was obtained during our studies, which we identified as the correct structure of ocellapyrone A. (C) 2007 Published by Elsevier Ltd.