Amat Mercedes, Lozano Oscar, Escolano Carmen, Molins Elies, Bosch Joan
Laboratory of Organic Chemistry, Faculty of Pharmacy, University of Barcelona, 08028-Barcelona, Spain.
J Org Chem. 2007 Jun 8;72(12):4431-9. doi: 10.1021/jo070397q. Epub 2007 May 9.
The stereochemical outcome of the enolate dialkylation of simple phenylglycinol-derived oxazolopiperidone lactams is studied. High stereoselectivities in the generation of the quaternary stereocenter are obtained by the appropriate choice of both the configuration of the starting lactam and the order of introduction of the substituents. The usefulness of the methodology is illustrated by the conversion of some of the dialkylated lactams into known synthetic precursors of alkaloids and by the total synthesis of (-)-quebrachamine.
研究了简单的苯基甘氨醇衍生的恶唑并哌啶酮内酰胺烯醇盐二烷基化的立体化学结果。通过适当选择起始内酰胺的构型和取代基引入顺序，在季碳立体中心的生成中获得了高立体选择性。通过将一些二烷基化内酰胺转化为已知的生物碱合成前体以及通过（-）-白坚木胺的全合成，说明了该方法的实用性。
