Radical carboazidation: expedient assembly of the core structure of various alkaloid families.
A procedure for one-pot intermolecular radical addition of 2-iodoesters to terminal alkenes followed by azidation of the radical adduct has been developed. This sequential reaction represents an alkene carboazidation process. Its efficacy is demonstrated by the two-step preparation of various lactams such as pyrrolidinones, pyrrolizidinones, and indolizidinones. An easy access to spirolactams bearing an amino-substituted quaternary carbon center is also described. These compounds are important building blocks for the synthesis of numerous alkaloids such as, for instance, FR901483.
Panchaud
Philippe
P
University of Berne, Department of Chemistry and Biochemistry, CH-3012 Berne, Switzerland.
Ollivier
Cyril
C
Renaud
Philippe
P
Zigmantas
Sarunas
S