Synthesis of (±) Peperomins

The total synthesis of natural antitumor agent (±) peperomin A, B and C are reported. These syntheses were started from benzophenones and diethyl succinate by Stobbe condensation. Three successive steps were employed to give the (±)-peperomins.     

Stobbe-like condensation reactions of the anion of diethyl (2-carboethoxy)benzylphosphonate with some aromatic and heterocyclic aldehydes

Deprotonation of diethyl (2-carboethoxy)benzylphosphonate using sodium ethoxide followed by reaction of the carbanion with furfural or aryl aldehydes gives diethyl (E)-1-(2′-carboxyphenyl)-1-phosphono-2-arylethenes that are formed via intramolecular Stobbe-like condensation reactions.     

Unexpected synthesis of a novel heterocyclic system – (7E,10aE)-2,7-Dimethylfuro[3′,4′:6,7]cycloocta[1,2,3-cd]indole-8,10(2H,6H)-dione

The first derivative of a novel heterocyclic system, (7E,10aE)-2,7-dimethylfuro[3′,4′:6,7]-cycloocta[1,2,3-cd]indole-8,10(2H,6H)-dione, was synthesized based on the Stobbe condensation of 3-chloro-1-methylindole-2-carbaldehyde with diethyl isopropylidenesuccinate. Cyclization of the 2-indolyl-containing diacid, formed by subsequent hydrolysis of the condensation product, did not lead to the expected fulgide, but rather to an unprecedented tetracyclic compound, the structure of which was established by ¹H, ¹³C NMR, IR spectroscopy, mass-spectrometry and single crystal X-ray diffraction.     

Threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成

报道了双木脂素threo-(±)-开环异落叶松脂醇二阿魏酸酯的全合成. 以香草醛为原料, 经过两步Stobbe反应构建木脂素骨架, 然后再用LiAlH₄还原、加氢后, 产物经柱层析分离, 得到2个异构体meso-和threo-(±)-开环落叶松脂素; 根据其NMR, IR和HRMS等谱图确认发现, 极性较小的产物threo-(±)-开环落叶松脂素为合成的关键中间体. threo-(±)-开环落叶松脂素与甲氧甲基(MOM)保护的阿魏酸缩合得到目标产物threo-(±)-开环异落叶松脂醇二阿魏酸酯. 合成采用汇聚法, 经11步, 以约8%的总产率得到了目标产物. 该合成方法具有原料价廉易得及操作简便的优点, 并具有一定的实用价值.     

丁烷型木脂素及衍生物的合成和生物活性

报道了一条合成丁烷木脂素的新路线. 以芳香醛为起始原料, Stobbe缩合和烷基化反应为关键步骤, 构建了木脂素骨架, 再经拆分及还原, 可得到相应的苏式和赤式异构体. 经官能团转化得到5个丁烷木脂素和8个丁醚木脂素, 其中3个天然产物为首次合成. 对合成产物进行抗HIV病毒和和抗疱疹病毒活性研究, 部分化合物显示出较高的抗病毒活性, 而且骨架构型对活性影响较大.     

Synthesis and application on parallel image storage of bisfurylfulgide

The synthesis of photochromic compounds has received a great deal of attention because of their potential application in various areas such as optical information storage[1—5], photoswitches and molecular recognition[6—8]. One of the most important researches in this field is the synthesis of a variety of photochromic fulgides to establish basic correlation between their molecular structures and photochromic properties. Since 1978, Heller[9] firstly reported the synthesis of the heterocyclic…     

An Efficient Synthetic Method of Nordihydroguaiaretic Acid（NDGA）

Nordihydroguaiaretic acid(NDGA)has been synthesized in nine steps from piperonal using Stobbe condensation as the key step with high yield.By this approach,five relative natural products were obtained.     

Facile Synthesis of 4-Oxo-4H-quinolizine-2-carboxamide Derivatives

A facile synthetic method for the construction of 2-substituted-4-oxo-4H-quinolizine-based core structure has been successfully developed. The synthesis made use of a one-pot Stobbe condensation followed by cyclization starting from the commercially available 2-pyridinecarbaldehyde. The structure of the formed 4-oxo-4H-quinolizine-2-carboxylate was fully confirmed by mass spectra, ¹H NMR and ¹³C NMR, correlation spectrography, heteronuclear multiple bond correlation, and heteronuclear single quantum coherence (HSQC) spectra. The ethyl carboxylate moiety was then further functionalized via direct aminolysis by a range of amines to afford the corresponding 4-oxo-4H-quinolizine-2-carboxamides 4a–i in moderate to good yields.