Multiple multicomponent macrocyclizations including bifunctional building blocks (MiBs) based on Staudinger and Passerini three-component reactions

J Org Chem. 2008 Mar 7;73(5):1762-7. doi: 10.1021/jo7022125. Epub 2008 Feb 2.

Abstract

Multiple multicomponent macrocyclizations including bifunctional buildings blocks (MiBs) so far have relied almost exclusively on Ugi reactions. The efficient expansion to non-Ugi-MiBs is exemplified by the synthesis of tetra-beta-lactam and bis-alpha-acyloxy carboxamide macrocycles based on multiple Staudinger and Passerini three-component reactions (3CR), respectively. A recent variation of the Passerini-3CR that involves primary alcohols, isocyanides, and carboxylic acids under oxidative conditions is successfully adapted to this procedure.

Publication types

  • Research Support, Non-U.S. Gov't

MeSH terms

  • Macrocyclic Compounds / chemistry*
  • Magnetic Resonance Spectroscopy
  • Spectrometry, Mass, Electrospray Ionization / methods*

Substances

  • Macrocyclic Compounds