Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamadaoka, Suita, Osaka 565-0871, Japan.
Org Biomol Chem. 2012 Nov 21;10(43):8609-15. doi: 10.1039/c2ob26532j.
A stereoconvergent access to chiral carbocyclic building blocks is reported. 6-(3'-Hydroxy-4'-methylpent-4'-enyl)-3-methoxy cyclohex-2-enone () that consists of four stereoisomers, i.e., racemic ca. 1 : 1 diastereomers, is converted to enantiomerically pure carbocycles through a combination of regioselective catalytic asymmetric reduction and alkylative remote stereoinduction. The present stereoconvergent strategy has allowed the formal synthesis of bioactive (-)-dysidiolide.
本文报道了一种手性碳环砌块的立体汇聚式方法。由四个立体异构体（即外消旋约 1:1 的非对映异构体）组成的 6-(3'-羟基-4'-甲基戊-4'-烯基)-3-甲氧基环己-2-烯酮 () 通过区域选择性催化不对称还原和烷基化远程立体诱导的组合，转化为对映体纯的碳环。本立体汇聚策略已实现了生物活性 (-)-dysidiolide 的形式合成。
