Recent developments in palladium-catalyzed carbonylation of steroids - An alternative approach to steroidal carbonyl compounds and carboxylic acid derivatives

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1 Citation (Scopus)

Abstract

There is an increasing interest in developing new strategies to introduce functional groups into specific positions of steroidal nuclei in order to modify their biological properties. Transition metal catalyzed reactions have proved to be versatile tools both for the construction of the steroid framework from easily available building blocks and for the functionalization of the steroidal skeleton. By palladium-catalyzed carbonylation, carbon monoxide can be introduced directly into a number of different sites in an organic molecule leading to the synthesis of aldehydes, ketones, carboxylic acids and their derivatives, lactones, lactames, etc. The products can often be obtained in good yield and with high selectivity usually under very mild conditions. In addition, palladium-catalyzed carbonylation is compatible with many functional groups, and therefore, more advantageous than conventional methods. In the present paper the most important achievements in carbonylation of steroidal substrates is reviewed together with a more detailed discussion of our own results obtained in this field.

Original languageEnglish
Pages (from-to)587-604
Number of pages18
JournalPolish Journal of Chemistry
Volume80
Issue number4
Publication statusPublished - Apr 2006

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Carbonylation
Carbonyl compounds
Palladium
Carboxylic Acids
Steroids
Derivatives
Functional groups
Lactones
Carbon Monoxide
Ketones
Aldehydes
Transition metals
Molecules
Substrates

Keywords

  • Alkenyl halide
  • Carbonylation
  • Enol triflate
  • Palladium catalysts
  • Steroids

ASJC Scopus subject areas

  • Chemistry(all)

Cite this

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abstract = "There is an increasing interest in developing new strategies to introduce functional groups into specific positions of steroidal nuclei in order to modify their biological properties. Transition metal catalyzed reactions have proved to be versatile tools both for the construction of the steroid framework from easily available building blocks and for the functionalization of the steroidal skeleton. By palladium-catalyzed carbonylation, carbon monoxide can be introduced directly into a number of different sites in an organic molecule leading to the synthesis of aldehydes, ketones, carboxylic acids and their derivatives, lactones, lactames, etc. The products can often be obtained in good yield and with high selectivity usually under very mild conditions. In addition, palladium-catalyzed carbonylation is compatible with many functional groups, and therefore, more advantageous than conventional methods. In the present paper the most important achievements in carbonylation of steroidal substrates is reviewed together with a more detailed discussion of our own results obtained in this field.",
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