Si Chang-Mei, Shao Lu-Ping, Mao Zhuo-Ya, Zhou Wen, Wei Bang-Guo
Department of Natural Products Chemistry, School of Pharmacy, Fudan University, 826 Zhangheng Road, Shanghai, 201203, China.
Org Biomol Chem. 2017 Jan 18;15(3):649-661. doi: 10.1039/c6ob02523d.
A diastereoselective approach to trans-4-hydroxy-5-substituted 2-pyrrolidinones 1 (P = TBS, P = H) has been developed through a stereoselective tandem Barbier process of (R,S)-8 with alkyl and aryl bromide. The stereochemistry at the C-5 stereogenic center of the trans-4-hydroxy-5-substituted 2-pyrrolidinones was solely controlled by α-alkoxy substitution. This effective approach was successfully used to prepare a variety of substituted (3R,4S)-statines 2. In addition, two bioactive natural products of (+)-preussin 4 and hapalosin 5 were effectively synthesized through this stereoselective tandem Barbier process.
通过(R,S)-8与烷基和芳基溴的立体选择性串联巴比耶反应，开发了一种合成反式-4-羟基-5-取代-2-吡咯烷酮1（P = TBS，P = H）的非对映选择性方法。反式-4-羟基-5-取代-2-吡咯烷酮C-5立体中心的立体化学仅由α-烷氧基取代控制。这种有效方法成功用于制备多种取代的(3R,4S)-司他汀2。此外，通过这种立体选择性串联巴比耶反应有效合成了两种生物活性天然产物(+)-前胡素4和哈帕洛辛5。
