8-iso-15(R)-prostaglandin F2α

• 分子结构分类: 有机化合物 - 脂质和类脂质分子 - 脂肪酰基
• 英文名称: 8-iso-15(R)-prostaglandin F2α
• 英文别名: 8-iso-15(R)-PGF_2α；15-epi-F_2t-isoprostane；15-epi-15-F2t-IsoP；(Z)-7-[(1S,2R,3R,5S)-3,5-dihydroxy-2-[(E,3R)-3-hydroxyoct-1-enyl]cyclopentyl]hept-5-enoic acid
• 化学式: C₂₀H₃₄O₅
• 分子量: 354.487
• InChiKey: PXGPLTODNUVGFL-PGWUFSIFSA-N

计算性质

• 辛醇/水分配系数(LogP)：
  2.7
• 重原子数：
  25
• 可旋转键数：
  12
• 环数：
  1.0
• sp3杂化的碳原子比例：
  0.75
• 拓扑面积：
  98
• 氢给体数：
  4
• 氢受体数：
  5

反应信息

• 作为产物：
  描述：

  ethyl (Z)-7-[(1S,2R,3R,5S)-3-acetyloxy-5-hydroxy-2-[(E,1S)-1-phenylsulfanyloct-2-enyl]cyclopentyl]hept-5-enoate 在 lithium hydroxide 、 sodium tetrahydroborate 、 间氯过氧苯甲酸 、 2,3-二氯-5,6-二氰基-1,4-苯醌 、 三甲氧基磷 作用下， 以 四氢呋喃 、 1,4-二氧六环 、 甲醇 、 二氯甲烷 、 水 为溶剂， 反应 22.5h， 生成 8-iso-15(R)-prostaglandin F2α
  参考文献：
  名称：

  15-F2t-异前列腺素的四种对映体纯的异构体的合成

  摘要：

  描述了15-F2t-异前列腺素的四种对映体纯的异构体的合成。关键步骤是由脂肪酶介导的拟内消旋二醇的拆分，以得到高对映体纯度的区域异构乙酸酯。还报道了用于制备假间消旋二醇的改进方法。

  DOI：

  10.1016/s0040-4020(98)83038-x

文献信息

• Stereocontrolled Access to Isoprostanes via a Bicyclo[3.3.0]octene Framework
  作者：Camille Oger、Yasmin Brinkmann、Samira Bouazzaoui、Thierry Durand、Jean-Marie Galano

  DOI：10.1021/ol802104z

  日期：2008.11.6

  stereocontrolled strategy toward the total synthesis of isoprostanes based on a bicyclic alpha,beta-epoxy ketone intermediate 6. Bicyclo[3.3.0]octene scaffold permitted stereodirection of reagents allowing stereoselective epoxidation, diastereoselective ketone reduction, and regioselective epoxide opening otherwise not accessible with a simple cyclopentene framework.

  我们报告了基于双环α，β-环氧酮中间体6的异丙醇全合成的简单且高度立体控制的策略。双环[3.3.0]辛烯骨架允许试剂的立体定向，从而允许立体选择性环氧化，非对映选择性酮还原和区域选择性环氧化物否则无法通过简单的环戊烯框架打开。
• Stereodivergent Synthesis of All 15-F₂ Isoprostanes
  作者：Thomas O. Schrader、Marc L. Snapper

  DOI：10.1021/ja027154u

  日期：2002.9.1

  Isoprostanes, lipid metabolites generated from free radical oxidation of membrane-bound arachidonic acid, have been detected in organisms subjected to oxidative stress; however, the function and cellular targets of the isoprostanes are unclear. As an initial step toward studying the biological role of these molecules, we report the preparation of all known and anticipated 15-F2 isoprostanes. The stereodivergent strategy to the complete isoprostane library features a ring-opening metathesis to introduce the cis-alkyl side chains that are characteristic of this class of molecules. Resolution to the individual stereoisomers can be accomplished by either a catalytic asymmetric reduction or an auxiliary-based separation protocol. In either case, the individual isomers can be converted to the corresponding 15-F2 isoprostanes through a straightforward functionalization of the carboxylic acid-containing side chain. The availability of this complete 15-F2 isoprostane library, containing both known and anticipated lipid metabolites, allows for the first time the side-by-side evaluation of these compounds in a variety of biological assays.
• Synthesis of the four enantiomerically-pure isomers of 15-F2t-isoprostane
  作者：Douglass F. Taber、Kazuo Kanai

  DOI：10.1016/s0040-4020(98)83038-x

  日期：1998.9

  Syntheses of the four enantiomerically-pure isomers of 15-F2t-isoprostane are described. The key step is the lipase-mediated resolution of a pseudo-meso diol, to give the regioisomeric acetates in high enantiomeric purity. Improved procedures for the preparation of the pseudo-meso diol are also reported.

  描述了15-F2t-异前列腺素的四种对映体纯的异构体的合成。关键步骤是由脂肪酶介导的拟内消旋二醇的拆分，以得到高对映体纯度的区域异构乙酸酯。还报道了用于制备假间消旋二醇的改进方法。