Gold-catalyzed cyclizations of alkynol-based compounds: synthesis of natural products and derivatives

Molecules. 2011 Sep 13;16(9):7815-43. doi: 10.3390/molecules16097815.

Abstract

The last decade has witnessed dramatic growth in the number of reactions catalyzed by gold complexes because of their powerful soft Lewis acid nature. In particular, the gold-catalyzed activation of propargylic compounds has progressively emerged in recent years. Some of these gold-catalyzed reactions in alkynes have been optimized and show significant utility in organic synthesis. Thus, apart from significant methodology work, in the meantime gold-catalyzed cyclizations in alkynol derivatives have become an efficient tool in total synthesis. However, there is a lack of specific review articles covering the joined importance of both gold salts and alkynol-based compounds for the synthesis of natural products and derivatives. The aim of this Review is to survey the chemistry of alkynol derivatives under gold-catalyzed cyclization conditions and its utility in total synthesis, concentrating on the advances that have been made in the last decade, and in particular in the last quinquennium.

Publication types

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

MeSH terms

  • Alkynes / chemical synthesis*
  • Alkynes / chemistry
  • Biological Products / chemical synthesis*
  • Catalysis
  • Chemistry Techniques, Synthetic / methods
  • Cyclization
  • Gold / chemistry*
  • Ketones / chemical synthesis*
  • Ketones / chemistry

Substances

  • Alkynes
  • Biological Products
  • Ketones
  • Gold