methyl 13,14,15,16-tetranorlabd-6-ene-12,8β-olide-19-oate | 55050-21-0

• 分子结构分类: 有机化合物 - 有机杂环化合物 - 萘并呋喃类
• 英文名称: methyl 13,14,15,16-tetranorlabd-6-ene-12,8β-olide-19-oate
• 英文别名: methyl (3aS,5aR,6S,9aS,9bR)-3a,6,9a-trimethyl-2-oxo-1,5a,7,8,9,9b-hexahydrobenzo[e][1]benzofuran-6-carboxylate
• CAS: 55050-21-0
• 化学式: C₁₇H₂₄O₄
• 分子量: 292.375
• InChiKey: KRYGNOIQTMAIDR-XYFLEOOXSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.9
• 重原子数：
  21
• 可旋转键数：
  2
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.76
• 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：

  methyl 13,14,15,16-tetranorlabd-6-ene-12,8β-olide-19-oate 在 lithium aluminium tetrahydride 、 silica gel 作用下， 以 四氢呋喃 为溶剂， 生成 2-((2aS,5aR,6S,8aR,8bR)-2a,5a,7-Trimethyl-2a,3,4,5,5a,6,8a,8b-octahydro-2H-naphtho[1,8-bc]furan-6-yl)-ethanol
  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：

  8-oxo-13,14,15,16,17-pentanorlabdane-12,19-dioic acid 在 苯基氯化硒 作用下， 以 四氢呋喃 、 正己烷 、 乙酸乙酯 为溶剂， 反应 60.58h， 生成 methyl 13,14,15,16-tetranorlabd-6-ene-12,8β-olide-19-oate
  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

• 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.