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Photooxygenation of Furylalkylamines: Easy Access to Pyrrolizidine and Indolizidine Scaffolds
Author(s) -
Kalaitzakis Dimitris,
Triantafyllakis Myron,
Sofiadis Manolis,
Noutsias Dimitris,
Vassilikogiannakis Georgios
Publication year - 2016
Publication title -
angewandte chemie
Language(s) - English
Resource type - Journals
eISSN - 1521-3757
pISSN - 0044-8249
DOI - 10.1002/ange.201600988
Subject(s) - photooxygenation , pyrrolizidine , indolizidine , chemistry , combinatorial chemistry , nanotechnology , stereochemistry , organic chemistry , materials science , singlet oxygen , oxygen , alkaloid
Abstract A highly adaptable method targeting the ubiquitous and very important pyrrolizidine and indolizidine scaffolds is presented. The general synthetic utility of the method is underscored by its application to the rapid and easy synthesis of five natural products starting from readily accessible alkylfuran precursors. These unprotected primary furylalkylamines are subjected to photooxygenation conditions, which initiate a complex cascade reaction sequence concluding with the production of high value motifs. This sequence can be tailored to need by varying the choice of both photosensitizer and base additive.