13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid | 291748-34-0

• 分子结构分类: 有机化合物 - 有机酸及其衍生物 - 羧酸及其衍生物
• 英文名称: 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid
• 英文别名: (1S,4aR,5S,8aR)-5-(carboxymethyl)-1,4a-dimethyl-6-methylidene-3,4,5,8a-tetrahydro-2H-naphthalene-1-carboxylic acid
• CAS: 291748-34-0
• 化学式: C₁₆H₂₂O₄
• 分子量: 278.348
• InChiKey: QXKIDQXMALJGHQ-OJDYBEQGSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.6
• 重原子数：
  20
• 可旋转键数：
  3
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.62
• 拓扑面积：
  74.6
• 氢给体数：
  2
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid 在 palladium diacetate 、 对苯醌 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 正己烷 、 溶剂黄146 、 丙酮 为溶剂， 反应 168.66h， 生成 (1R,2R,9R,12S,16R)-1,12-dimethyl-4-trimethylsilyloxy-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadeca-3,7-dien-11-one
  参考文献：
  名称：

  First Synthesis of the Antifungal Oidiolactone C from trans-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds

  摘要：

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.

  DOI：

  10.1021/jo0161882
• 作为产物：
  描述：

  (10S,3R,5R,6R)-10-(Methoxycarbonyl)-5-[(methoxycarbonyl)methyl]-6,10-dimethyl-4-methylenebicyclo[4.4.0]dec-3-yl 2,2,2-trifluoroacetate 在 四(三苯基膦)钯 potassium carbonate 、 1-丙烷硫醇钠 作用下， 以 N,N-二甲基甲酰胺 、 甲苯 为溶剂， 反应 33.0h， 生成 13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid
  参考文献：
  名称：

  Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C

  摘要：

  A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic trifluoroacetates and Pd-catalysed bislactonisation as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.

  DOI：

  10.1016/s0040-4039(00)00815-7

文献信息

• Preparation of bioactive podolactones via a new Pd-catalysed bislactonisation reaction. Synthesis of oidiolactone C
  作者：Alejandro F Barrero、José F Quı́lez Del Moral、Juan M Cuerva、E Cabrera、David Jiménez-González

  DOI：10.1016/s0040-4039(00)00815-7

  日期：2000.7

  A new route towards podolactone skeleton compounds, including the recently discovered Oidiolactone C, is described, using Pd-catalysed elimination of allylic trifluoroacetates and Pd-catalysed bislactonisation as key steps. (C) 2000 Elsevier Science Ltd. All rights reserved.
• First Synthesis of the Antifungal Oidiolactone C from <i>trans</i>-Communic Acid:  Cytotoxic and Antimicrobial Activity in Podolactone-Related Compounds
  作者：Alejandro F. Barrero、Siméon Arseniyadis、José F. Quílez del Moral、M. Mar Herrador、M. Valdivia、D. Jiménez

  DOI：10.1021/jo0161882

  日期：2002.4.1

  The synthesis of the fungicide oidiolactone C starting from diterpenic trans-communic acid was carried out with an overall yield of 11.7%. The key step in the process consists of a new bislactonization reaction catalyzed by Pd(H), which gives rise to the podolactone-type tetracyclic skeleton from a norlabdadienedioic acid. We also carried out a study of the structure-biological activity of different natural podolactones and their synthetic precursors. Thus, the highest cytotoxic activity was found in dienic dilactones with ether-type substitutions on C-17, whereas the closure of the gamma-lactone ring is not critical for presenting a maximal antimicrobial activity.