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

Claudia W. Roberson, Keith Woerpel

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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

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Silanes
Stereoselectivity
Alkaloids
Stereochemistry
peduncularine
chlorosulfonyl isocyanate

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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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.",
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