Radical azidation reactions and their application in the synthesis of alkaloids

Lapointe, Guillaume; Kapat, Ajoy; Weidner, Karin; Renaud, Philippe

doi:10.1351/PAC-CON-11-11-21

Pure Appl. Chem., 2012, Vol. 84, No. 7, pp. 1633-1641

http://dx.doi.org/10.1351/PAC-CON-11-11-21

Published online 2012-05-27

Radical azidation reactions and their application in the synthesis of alkaloids

Guillaume Lapointe, Ajoy Kapat, Karin Weidner and Philippe Renaud*

Department of Chemistry and Biochemistry, University of Bern, Freiestrasse 3, CH-3012 Bern, Switzerland

Abstract: Recent advances in radical azidation using sulfonyl azides are presented. For instance, radical carboazidation using α-iodoketones, desulfitative carboazidation, and anti-Markovnikov hydroazidation of alkenes are described. These novel methods tolerate a large number of functional groups and allow the synthesis of organic azides that would be difficult to synthesize otherwise. The transformation of the azides using reductive processes as well as a Schmidt reaction under nonacidic conditions were used to synthesize alkaloids including indolizidine 167B, monomorine I, cylindricine C, and lepadiformine C.