Quan Long Guo, Cha Jin Kun
Department of Chemistry, University of Alabama, Tuscaloosa, AL 35487, USA.
Chem Phys Lipids. 2004 Mar;128(1-2):3-14. doi: 10.1016/j.chemphyslip.2003.10.005.
This review delineates several reported methods for the synthesis of isoprostanes and neuroprostanes with particular emphasis on the stereocontrolled construction of a suitably functionalized cyclopentane core. The alpha- and omega-side chains of these PG-like molecules are typically assembled by Wittig-type olefination reactions, standard transformations in the PG synthesis. The synthetic strategies include free radical cyclizations, a palladium-promoted coupling of three different components, an intramolecular cyclopropanation reaction-ring-opening sequence, a [2+2] photocycloaddition-ring-opening metathesis approach, and an intramolecular cross-coupling reaction of an alkyl iodide and a tethered alkenylsiloxane.
本综述阐述了几种已报道的异前列腺素和神经前列腺素的合成方法，特别强调了具有适当官能化的环戊烷核心的立体控制构建。这些类前列腺素分子的α-和ω-侧链通常通过维蒂希型烯烃化反应组装，这是前列腺素合成中的标准转化反应。合成策略包括自由基环化、钯促进的三种不同组分的偶联、分子内环丙烷化反应-开环序列、[2+2]光环加成-开环复分解方法以及烷基碘与连接的烯基硅氧烷的分子内交叉偶联反应。
