Graduate School of Pharmaceutical Sciences, Osaka University, 1-6 Yamada-oka, Suita, Osaka, 565-0871 Japan.
Org Lett. 2012 Feb 17;14(4):1054-7. doi: 10.1021/ol203425p. Epub 2012 Feb 8.
The iodocyclization of γ,δ-unsaturated alcohols in the presence of a silyl enol ether produced cis-2,5-disubstituted tetrahydrofurans in one pot via siloxy intermediates. N-Iodosuccinimide (NIS) effectively worked as an activator of the double bonds in the substrates and the silyl enol ether. Application to an expedient synthesis of the adjacent bis-tetrahydrofuran core of Annonaceous acetogenins with a cis/threo/cis relative stereochemistry is also described.
在硅基烯醇醚的存在下，γ,δ-不饱和醇的碘环化反应一锅法生成顺式-2,5-二取代的四氢呋喃，通过硅氧基中间体。N-碘代丁二酰亚胺（NIS）有效地作为底物和硅基烯醇醚中双键的活化剂。还描述了其在具有顺式/苏式/顺式相对立体化学的番荔枝烷酮的相邻双四氢呋喃核的便捷合成中的应用。
