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. (C) 2000 Elsevier Science Ltd.
All Science Journal Classification (ASJC) codes
- Drug Discovery
- Organic Chemistry