Acyl radical insertion for the direct formation of new seven-substituted pterin analogs

✍ Scribed by Jeff M. Pruet; Jon D. Robertus; Eric V. Anslyn

• Book ID: 104097597
• Publisher: Elsevier Science
• Year: 2010
• Tongue: French
• Weight: 135 KB
• Volume: 51
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/j.tetlet.2010.03.008

✦ Synopsis

A variety of pterin molecules were synthesized via an under-utilized acyl radical insertion, using aldehydes and a-keto esters as the acyl source. These reactions gave complete regiospecificity for the 7-isomer, with reaction times ranging in minutes, often with instantaneous product precipitation. This approach led to the construction of new pterin analogs unaccessible via traditional Friedel-Crafts acylation. The compounds were characterized by NMR spectroscopy and high-resolution mass spectroscopy.