Jacobo Sheila H, Chang Chih-Tsung, Lee Gue-Jae, Lawson John A, Powell William S, Pratico Domenico, FitzGerald Garret A, Rokach Joshua
Claude Pepper Institute and Department of Chemistry, Florida Institute of Technology, 150 West University Boulevard, Melbourne, Florida 32901, USA.
J Org Chem. 2006 Feb 17;71(4):1370-9. doi: 10.1021/jo051916x.
[reaction: see text] A new and stereoselective approach for the synthesis of all-syn isoprostanes is reported. This method, which is based on acid-catalyzed Diels-Alder reaction, allows the introduction of the side chain with a predetermined stereochemistry of the hydroxy group. The first total synthesis of an eicosapentaenoic acid (EPA)-derived iP, 8,12-iso-iPF3alpha-VI 10, was performed using this approach.
[反应：见正文] 报道了一种合成全顺式异前列腺素的新的立体选择性方法。该方法基于酸催化的狄尔斯-阿尔德反应，能够以预定的羟基立体化学引入侧链。使用该方法首次全合成了一种源自二十碳五烯酸（EPA）的异前列腺素，即8,12-异- iPF3α-VI 10。
