isoanticopal-12-en-15-al | 870692-49-2

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 异戊烯醇脂质
• 英文名称: isoanticopal-12-en-15-al
• 英文别名: (1R,4aR,4bS,8aS,10aR)-2,4b,8,8,10a-pentamethyl-4,4a,5,6,7,8a,9,10-octahydro-1H-phenanthrene-1-carbaldehyde
• CAS: 870692-49-2
• 化学式: C₂₀H₃₂O
• 分子量: 288.473
• InChiKey: YLIFITFVWRKVSD-ORZNMBHWSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  5.7
• 重原子数：
  21
• 可旋转键数：
  1
• 环数：
  3.0
• sp3杂化的碳原子比例：
  0.85
• 拓扑面积：
  17.1
• 氢给体数：
  0
• 氢受体数：
  1

反应信息

• 作为反应物：
  描述：

  isoanticopal-12-en-15-al 在 对甲苯磺酸 、 lithium diisopropyl amide 作用下， 以 四氢呋喃 、 六甲基磷酰三胺 、 苯 为溶剂， 反应 2.33h， 生成 (14R)-ent-isocopal-13(16)-en-15-al
  参考文献：
  名称：

  Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide

  摘要：

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.

  DOI：

  10.1021/jo0515529
• 作为产物：
  描述：

  (10S,14R)-(-)-isoagath-12-en-15-ol 在 四丙基高钌酸铵 、 N-甲基吗啉氧化物 作用下， 以 二氯甲烷 为溶剂， 以95 %的产率得到isoanticopal-12-en-15-al
  参考文献：
  名称：

  通过生物催化多烯环化化学酶法合成 (+)-isoagatholactone、(+)-spongi-16-one 和 3-deoxychavalone A

  摘要：

  研究了角鲨烯-藿烯环化酶（SHC）催化香叶基香叶醇的立体选择性环化反应。通过该转化，以简洁且氧化还原经济的方式合成了海绵二萜(+)-isoagatholactone和(+)-spongi-16-one，以及类萜3-脱氧查瓦酮A。这项工作展示了 SHC 催化环化作为萜类化合物合成关键步骤的应用。

  DOI：

  10.1039/d3ob00206c

文献信息

• The first synthesis of marine sesterterpene (+)-scalarolide
  作者：Xiang-Jian Meng、Yang Liu、Wen-Yuan Fan、Bin Hu、Wenting Du、Wei-Ping Deng

  DOI：10.1016/j.tetlet.2009.06.064

  日期：2009.9

  The synthesis of the first example of C12 oxygenated marine scalaranic sesterterpenes (+)-scalarolide was achieved through three key steps including the ring-opening rearrangement of epoxide, stereoselective Diels-Alder addition and one-pot gamma-butenolide formation process, and the absolute configuration of natural scalarolide was confirmed. (C) 2009 Elsevier Ltd. All rights reserved.
• Synthesis of spongidines A and D: marine metabolites phospholipase A2 inhibitors
  作者：P. Basabe、A. Blanco、I.S. Marcos、D. Díez、O. Bodero、M. Martín、J.G. Urones

  DOI：10.1016/j.tet.2011.03.084

  日期：2011.5

  Two different strategies for the synthesis of spongidines A and D are presented. Herein we describe a route based in an amino acid insertion followed by aromatization. Another alternative is the construction of a pyridine derivative followed by N-alkylation. Both methodologies have intermediate 5 as a key compound, which is eventually accessible from methyl isoanticopalate. (C) 2011 Elsevier Ltd. All rights reserved.
• Synthesis of (+)-makassaric acid, a protein kinase MK2 inhibitor
  作者：P. Basabe、M. Martín、O. Bodero、A. Blanco、I.S. Marcos、D. Díez、J.G. Urones

  DOI：10.1016/j.tet.2010.06.023

  日期：2010.8

  Description of the first synthesis of (+)-makassaric acid, an important kinase MK2 inhibitor. The key step was a Barton/McCombie radical deoxygenation. (c) 2010 Elsevier Ltd. All rights reserved.
• Synthesis of Three Marine Natural Sesterterpenolides from Methyl Isoanticopalate. First Enantioselective Synthesis of Luffolide
  作者：P. Basabe、S. Delgado、I. S. Marcos、D. Diez、A. Diego、M. De Román、J. G. Urones

  DOI：10.1021/jo0515529

  日期：2005.11.1

  The synthesis of three marine sponge metabolites, luffolide (4), 5, and 6, are described for the first time, establishing the absolute configuration of these compounds. The key intermediate, aldehyde 17, wash obtained from methyl isoanticopalate, 11. The addition of 3-furyllithium to 17 and subsequent photochemical oxidation give the gamma-hydroxybutenolide 5 and its epimer at C-16. Sesterterpenolide 6 is obtained by dehydration of 5. From the key aldehyde 17, luffolide (4) was obtained in six steps.
• Chemoenzymatic synthesis of (+)-isoagatholactone, (+)-spongian-16-one, and 3-deoxychavalone A <i>via</i> biocatalytic polyene cyclization
  作者：Wen Xiao、Su-Jing Wang、Ming-Zhu Yu、Xue-Jie Zhang、Zheng Xiang

  DOI：10.1039/d3ob00206c

  日期：——

  The stereoselective cyclization of geranylgeraniol catalysed by squalene-hopene cyclase (SHC) was investigated. By use of this transformation, spongiane diterpenoids (+)-isoagatholactone and (+)-spongian-16-one, and meroterpenoid 3-deoxychavalone A were synthesized in a concise and redox-economic manner. This work showcases the application of SHC-catalysed cyclization as a key step in terpenoid synthesis

  研究了角鲨烯-藿烯环化酶（SHC）催化香叶基香叶醇的立体选择性环化反应。通过该转化，以简洁且氧化还原经济的方式合成了海绵二萜(+)-isoagatholactone和(+)-spongi-16-one，以及类萜3-脱氧查瓦酮A。这项工作展示了 SHC 催化环化作为萜类化合物合成关键步骤的应用。