A mild new procedure for production, cyclization and trapping of amidyl radicals: application to a formal total synthesis of peduncularine

✍ Scribed by Xichen Lin; Didier Stien; Steven M Weinreb

• Book ID: 104210070
• Publisher: Elsevier Science
• Year: 2000
• Tongue: French
• Weight: 134 KB
• Volume: 41
• Category: Article
• ISSN: 0040-4039
• DOI: 10.1016/s0040-4039(00)00194-5

✦ Synopsis

Treatment of an olefinic hydroxamic acid with tert-butylsulfinyl chloride and Hunig's base from -50°C to room temperature in the presence of a radical trap such as diphenyl diselenide, diphenyl disulfide or TEMPO affords a functionalized product derived from an amidyl radical cyclization. The methodology has been used in a formal total synthesis of the 6-azabicyclo[3.2.1]octane-containing indole alkaloid peduncularine.