Research Group of Organic Chemistry, Departments of Chemistry and Bio-Engineering Sciences, Vrije Universiteit Brussel , Pleinlaan 2, B-1050 Brussels, Belgium.
Institute of Organic Chemistry, Polish Academy of Sciences , Kasprzaka Strasse 44/52, 01-224 Warsaw, Poland.
Org Lett. 2015 Sep 18;17(18):4482-5. doi: 10.1021/acs.orglett.5b02145. Epub 2015 Aug 31.
A new convenient, mild, one-pot procedure is described for the diastereoselective synthesis of constrained 7,5- and 7,6-fused azabicycloalkanes. Using 2-formyl-L-tryptophan and 2-formyl-l-phenylalanine as bielectrophilic building blocks, T3P-mediated Pictet-Spengler and Meyers lactamization reactions were developed to present chiral and polycyclic aminoindolo- and aminobenzazepinone compounds in excellent yields. The conformationally constrained compounds can serve as templates for peptidomimetic research or polyheterocyclic privileged scaffolds.
描述了一种新的方便、温和、一锅法的方法，用于非对映选择性合成约束的 7,5-和 7,6-稠合氮杂双环烷。使用 2-甲酰基-L-色氨酸和 2-甲酰基-L-苯丙氨酸作为双亲电构建块，开发了 T3P 介导的 Pictet-Spengler 和 Meyers 内酰胺化反应，以优异的产率呈现手性和多环氨基吲哚和氨基苯并氮杂卓酮化合物。构象约束化合物可用作肽模拟研究或多杂环特权支架的模板。
