Formal synthesis of (±)-peduncularine: Use of the [3 + 2] annulation of allylic silanes and chlorosulfonyl isocyanate

Claudia W. Roberson, K. A. Woerpel

Research output: Contribution to journalArticlepeer-review

Abstract

(equation presented) The formal synthesis of the alkaloid (±)-peduncularine (1) was accomplished through the use of a [3 + 2] allylic silane annulation. The annulation of cyclohexadienyl silane 6 with chlorosulfonyl isocyanate followed by an in situ reduction provided bicyclic lactam 7. Conversion of this intermediate to 2 in three steps completed the formal synthesis of (±)-peduncularine.

Original languageEnglish (US)
Pages (from-to)621-622
Number of pages2
JournalOrganic Letters
Volume2
Issue number5
DOIs
StatePublished - Mar 9 2000

ASJC Scopus subject areas

  • Biochemistry
  • Physical and Theoretical Chemistry
  • Organic Chemistry

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