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

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• 作者：Mouhamad Jida ; Olivier Van der Poorten ; Karel Guillemyn ; Zofia Urbanczyk-Lipkowska ; Dirk Tourw茅 ; Steven Ballet
• 刊名：Organic Letters
• 出版年：2015
• 出版时间：September 18, 2015
• 年：2015
• 卷：17
• 期：18
• 页码：4482-4485
• 全文大小：371K
• ISSN：1523-7052

文摘

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鈥揝pengler 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.