T3P 促进的立体选择性皮克特-斯宾格勒和迈尔斯环化反应温和一锅法合成约束多环内酰胺二肽类似物。

T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet-Spengler and Meyers Lactamization Reactions.

机构信息

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.

出版信息

Org Lett. 2015 Sep 18;17(18):4482-5. doi: 10.1021/acs.orglett.5b02145. Epub 2015 Aug 31.

DOI:10.1021/acs.orglett.5b02145

PMID:26322913

Abstract

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.

摘要

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。