Department of Chemistry, University of Saskatchewan, Saskatoon, SK S7N 5C9, Canada.
Chem Commun (Camb). 2011 Nov 7;47(41):11375-93. doi: 10.1039/c1cc13323c. Epub 2011 Jul 15.
The strategic use of thiopyran templates to facilitate polypropionate synthesis was first demonstrated in Woodward's landmark total synthesis of erythromycin A in 1981 where the topology of a fused bicyclic system was exploited. In the ensuing three decades, various alternative strategic applications of thiopyran motifs to achieve key stereoselective transformations have emerged including, inter alia, unique substrates for chemoenzymatic syntheses, surrogates for 3-pentanone in enantioselective aldol reactions, and templates for enantiotopic group selective reactions. This review summarizes these developments.
噻吩模板的战略应用首次在伍德沃德 1981 年具有里程碑意义的红霉素 A 全合成中得到证明，其中利用了稠合双环系统的拓扑结构。在随后的三十年中，噻吩基序的各种替代战略应用已经出现，以实现关键的立体选择性转化，包括化学酶合成的独特底物、对映选择性羟醛反应中 3-戊酮的替代物以及对映体选择性基团选择性反应的模板。这篇综述总结了这些发展。
