Application of the intramolecular PIFA-mediated amidation of alkynes to the synthesis of substituted indolizidinones |
| |
Authors: | Leticia M. Pardo Imanol Tellitu Esther Domínguez |
| |
Affiliation: | Departamento de Química Orgánica II, Facultad de Ciencia y Tecnología (ZTF/FCT), Universidad del País Vasco/Euskal Herriko Unibertsitatea (UPV/EHU), PO Box 644, 48080 Bilbao, Spain |
| |
Abstract: | The construction of the title compounds has been achieved from properly substituted linear alkynylamides through the suitable combination of two key cyclization steps. First, an intramolecular PIFA-mediated alkyne amidation protocol leads to the creation of the pyrrolidinone nucleus, which under proper manipulation of the generated keto–carbonyl group permits the assembling of the indolizidinone skeleton by the introduction of a subsequent ring closing olefin metathesis step. Finally, its transformation into a series of substituted mono- and trihydroxylated indolizidinone derivatives is achieved by manipulation of the remaining unsaturated fragment under hydrogenation and dihydroxylation conditions. |
| |
Keywords: | |
本文献已被 ScienceDirect 等数据库收录! |
|