Tang Minyan, Pyne Stephen G
Department of Chemistry, University of Wollongong, Wollongong, New South Wales 2522, Australia.
J Org Chem. 2003 Oct 3;68(20):7818-24. doi: 10.1021/jo034914q.
A diastereoselective and modular approach to the synthesis of the 3-hydroxymethyl-2,3,5,6,7,7a-hexahydro-1H-pyrrolizine-1,2,7-triol structure, characteristic of several natural pyrrolizidine natural products, has been developed. This approach culminated in the synthesis of (-)-7-epiaustraline and (+)-1,7-diepiaustraline. The oxazolidinone group has been found to be a useful protecting group in the RCM reaction and, as part of a pyrrolo[1,2-c]oxazol-3-one ring system, has functioned as a stereo- and regio-directing group in a key diastereoselective cis-dihydroxylation reaction and a regioselective nucleophilic ring-opening of a S,S-dioxo-dioxathiole.
已开发出一种非对映选择性且模块化的方法来合成3-羟甲基-2,3,5,6,7,7a-六氢-1H-吡咯里西啶-1,2,7-三醇结构，该结构是几种天然吡咯里西啶天然产物的特征。此方法最终合成了(-)-7-表澳大利亚碱和(+)-1,7-二表澳大利亚碱。已发现恶唑烷酮基团在RCM反应中是一种有用的保护基团，并且作为吡咯并[1,2-c]恶唑-3-酮环系统的一部分，在关键的非对映选择性顺式二羟基化反应和S,S-二氧代-二氧硫杂环戊烷的区域选择性亲核开环反应中起到了立体和区域导向基团的作用。
