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

Xichen Lin, Didier Stien, Steven M. Weinreb

Research output: Contribution to journalArticlepeer-review

48 Scopus citations

Abstract

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.

Original languageEnglish (US)
Pages (from-to)2333-2337
Number of pages5
JournalTetrahedron Letters
Volume41
Issue number14
DOIs
StatePublished - Apr 1 2000

All Science Journal Classification (ASJC) codes

  • Biochemistry
  • Drug Discovery
  • Organic Chemistry

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