2-epi-amphidinolide E

• 分子结构分类: 有机化合物 - 苯丙烷和聚酮 - 大环内酯类和类似物
• 英文名称: 2-epi-amphidinolide E
• 英文别名: (1S,2R,3R,6S,7E,9E,11R,12R,13E,17S)-2,11,12-trihydroxy-6-methyl-3-[(2R,5E)-8-methyl-4-methylidenenona-5,8-dien-2-yl]-4,20-dioxabicyclo[15.2.1]icosa-7,9,13-trien-5-one
• 化学式: C₃₀H₄₄O₆
• 分子量: 500.676
• InChiKey: JGRAKHHMDYESEH-LAXYRQHISA-N

计算性质

• 辛醇/水分配系数(LogP)：
  6.2
• 重原子数：
  36
• 可旋转键数：
  6
• 环数：
  2.0
• sp3杂化的碳原子比例：
  0.57
• 拓扑面积：
  96.2
• 氢给体数：
  3
• 氢受体数：
  6

反应信息

• 作为产物：
  描述：

  (4R,5S)-4-methyl-3-((E)-(R)-2-methyl-hexa-3,5-dienoyl)-5-phenyl-oxazolidin-2-one 在 Grubbs catalyst first generation Bu3SnAlEt2 、 溶剂黄146 作用下， 以 四氢呋喃 、 正己烷 、 二氯甲烷 、 水 、 甲苯 为溶剂， 反应 53.0h， 生成 2-epi-amphidinolide E
  参考文献：
  名称：

  Total synthesis of amphidinolide E and amphidinolide E stereoisomers

  摘要：

  Four amphidinolide E stereoisomers, amphidinolide E (1), 2-epi-amphidinolide E (2), 19-epi-amphidinolide E (3), and 2-epi-19-epi- amphidinolide E (4), have been synthesized via the judicious union of aldehyde 5, allylsilanes 7 or 8, acids 9 or 10, and vinylstannane 6. The C19 stereocenters of the C19 epimeric allylsilanes 7 and 8 were introduced via crotylboration reactions early in the synthesis. [3+2] Annulation reactions of aldehyde 5 with allylsilanes 7 and 8 were employed to set the core tetrahydrofuran units of 1-4. Finally, the C2 stereo-center was installed by esterification using acid 9, without incident, or with acid 10, in which case an unexpected and completely stereoselective inversion of C2 occurs. (C) 2007 Elsevier Ltd. All rights reserved.

  DOI：

  10.1016/j.tet.2007.02.058

文献信息

• Synthesis of 2-<i>epi</i>-Amphidinolide E:  An Unexpected and Highly Selective C(2) Inversion during an Esterification Reaction
  作者：Porino Va、William R. Roush

  DOI：10.1021/ol0628098

  日期：2007.1.1

  A synthesis of 2-epi-amphidinolide E (1) has been accomplished via an unexpected and highly diastereoselective C(2) stereochemical inversion during the modified Yamaguchi esterification of alcohol 4b and Fe(CO)3-complexed dienoic acid 7. [reaction: see text].

  在修饰的山口酯化酒精4b和Fe（CO）3-复合二烯酸7的过程中，通过意外的且高度非对映选择性的C（2）立体化学转化，完成了2-表-氨基吡啶E（1）的合成。见文字]。