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

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T3P-Promoted, Mild, One-Pot Syntheses of Constrained Polycyclic Lactam Dipeptide Analogues via Stereoselective Pictet–Spengler and Meyers Lactamization Reactions
Organic Letters ( IF 4.9 ) Pub Date : 2015-08-31 00:00:00 , DOI: 10.1021/acs.orglett.5b02145
Mouhamad Jida ₁ , Olivier Van der Poorten ₁ , Karel Guillemyn ₁ , Zofia Urbanczyk-Lipkowska ₂ , Dirk Tourwé ₁ , Steven Ballet ₁

Affiliation

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.

中文翻译：

T3P促进的，通过立体选择性Pictet-Spengler和Meyers内酰胺化反应约束的多环内酰胺二肽类似物的温和一锅合成

描述了一种新的方便，温和的一锅法，用于受约束的7,5-和7,6-稠合的氮杂双环烷烃的非对映选择性合成。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子构件，开发了T3P介导的Pictet-Spengler和Meyers内酰胺化反应，以优异的产率提供了手性和多环氨基吲哚-和氨基苯并ze庚酮化合物。构象受限的化合物可以用作拟肽研究或多杂环特权支架的模板。

更新日期：2015-08-31

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