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

J Am Chem Soc. 2002 Sep 25;124(38):11342-8. doi: 10.1021/ja012152f.

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.

Publication types

  • Research Support, Non-U.S. Gov't
  • Research Support, U.S. Gov't, Non-P.H.S.

MeSH terms

  • Alkaloids / chemical synthesis*
  • Cyclohexanes / chemistry*
  • Cyclohexenes
  • Indole Alkaloids
  • Indoles / chemical synthesis*
  • Isocyanates / chemistry*
  • Plants / chemistry
  • Silanes / chemistry*
  • Stereoisomerism

Substances

  • Alkaloids
  • Cyclohexanes
  • Cyclohexenes
  • Indole Alkaloids
  • Indoles
  • Isocyanates
  • Silanes
  • peduncularine
  • cyclohexene