Photooxygenation of Furylalkylamines: Easy Access to Pyrrolizidine and Indolizidine Scaffolds

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.This is the accepted version of the following article: Angewandte Chem. Int. Ed. 2016, 55, 4605 – 4609, which has been published in final form at http://onlinelibrary.wiley.com/doi/10.1002/anie.201600988/abstract. This article may be used for non-commercial purposes in accordance with the Wiley Self-Archiving Policy