Silva Siguara Bastos Lemos, Torre Adriana Della, de Carvalho João Ernesto, Ruiz Ana Lúcia Tasca Gois, Silva Luiz F
Departamento de Química Fundamental, Instituto de Química, Universidade de São Paulo, Av. Prof. Lineu Prestes, 748, CP 26077, São Paulo-SP CEP 05513-970, Brazil.
Division of Pharmacology and Toxicology, Multidisciplinary Center for Chemical, Biological and Agricultural, State University of Campinas, 6171, Campinas-SP CEP 13081-970, Brazil.
Molecules. 2015 Jan 15;20(1):1475-94. doi: 10.3390/molecules20011475.
A versatile and metal-free approach for the synthesis of carbocycles and of heterocycles bearing seven- and eight-membered rings is described. The strategy is based on ring expansion of 1-vinylcycloalkanols (or the corresponding silyl or methyl ether) mediated by the hypervalent iodine reagent HTIB (PhI(OH)OTs). Reaction conditions can be easily adjusted to give ring expansion products bearing different functional groups. A route to medium-ring lactones was also developed.
本文描述了一种通用的、无金属的方法来合成碳环以及含有七元环和八元环的杂环。该策略基于由高价碘试剂HTIB（PhI(OH)OTs）介导的1-乙烯基环烷醇（或相应的硅基或甲基醚）的扩环反应。反应条件可以很容易地进行调整，以得到带有不同官能团的扩环产物。还开发了一种合成中环内酯的路线。
