Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: Application to the total synthesis of (±)-peduncularine

Claudia W. Roberson, K. A. Woerpel

Research output: Contribution to journalArticle

Abstract

The synthesis of (±)-peduncularine was accomplished using the [3 + 2] annulation of an allylic silane with chlorosulfonyl isocyanate to assemble the bicyclic core of the alkaloid. The stereochemistry of the annulation product was employed to control the installation of the indolylmethyl side chain at C-7 with complete stereoselectivity.

Original languageEnglish (US)
Pages (from-to)11342-11348
Number of pages7
JournalJournal of the American Chemical Society
Volume124
Issue number38
DOIs
StatePublished - Sep 25 2002

ASJC Scopus subject areas

  • Catalysis
  • Chemistry(all)
  • Biochemistry
  • Colloid and Surface Chemistry

Fingerprint Dive into the research topics of 'Development of the [3 + 2] annulations of cyclohexenylsilanes and chlorosulfonyl isocyanate: Application to the total synthesis of (±)-peduncularine'. Together they form a unique fingerprint.

  • Cite this