13,14,15,16-tetranorlabd-7-en-(19,6β),(12,17)-diolide | 291748-35-1

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并吡喃类
• 英文名称: 13,14,15,16-tetranorlabd-7-en-(19,6β),(12,17)-diolide
• 英文别名: 13,14,15,16-tetranorlabd-7-ene-19,6b:12,17-diolide；13,14,15,16-tetranorlabd-7-en-16,6β:12,17-diolide；(1R,2R,9R,12S,16R)-1,12-dimethyl-5,10-dioxatetracyclo[7.6.1.02,7.012,16]hexadec-7-ene-4,11-dione
• CAS: 291748-35-1
• 化学式: C₁₆H₂₀O₄
• 分子量: 276.332
• InChiKey: KOIAEXUZBOCWNM-NAGUFLCVSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  1.8
• 重原子数：
  20
• 可旋转键数：
  0
• 环数：
  4.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  52.6
• 氢给体数：
  0
• 氢受体数：
  4

反应信息

• 作为反应物：
  描述：

  13,14,15,16-tetranorlabd-7-en-(19,6β),(12,17)-diolide 在 吡啶 、 双氧水 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 二氯甲烷 为溶剂， 反应 31.5h， 生成 CJ-14445
  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
• 作为产物：
  描述：

  13,14,15,16-tetranorlabda-6,8(17)-diene-12,19-dioic acid 在 4 A molecular sieve 、 碘 、 N,N'-羰基二咪唑 作用下， 以 乙腈 为溶剂， 反应 29.0h， 生成 13,14,15,16-tetranorlabd-7-en-(19,6β),(12,17)-diolide
  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

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.