Regio- and Enantioselective Functionalization of Acyclic Polyprenoids

Authors

  • Alejandro F. Barrero University of Granada
  • José F. Quílez del Moral University of Granada
  • María del Mar Herrador University of Granada
  • Elena M. Sánchez University of Granada
  • Jesús F. Arteaga University of Granada

Keywords:

Acyclic polyprenes, allylic functionalization, selenium dioxide, palladium, asymmetric dihydroxylation, terpenes

Abstract

Abstract. In this paper we present the results obtained in the positional selective functionalization of the double bond located at the terminal isopropylidene unit of acyclic polyprenoids. Studies to introduce the hydroxyl group or related oxygenated functions has been tested using oxidation with SeO2 or catalytic procedures employing Pd(II) catalysts. This functionalization is usually found in many natural or synthetic acyclic terpenes and would permit to carry out epoxydations regio- and stereoselectives. Furthermore, asymmetric dihydroxilation procedure has been optimized in different polyprenoids in order to generalize this methodology as the key step for the enantioselective synthesis of epoxides.

 

Resumen. En este trabajo presentamos los resultados obtenidos en la funcionalización posicional selectiva del doble enlace situado en el extremo terminal de la cadena en poliprenoides acíclicos. Los estudios para introducir un grupo hidroxilo o funciones oxigenadas relacionadas han sido realizados empleando SeO2 o un procedimiento catalítico en Pd(II). Esta funcionalización es frecuentemente encontrada en diferentes terpenos acíclicos naturales o sintéticos, y permite llevar a cabo epoxidaciones regio- y estereoselectivas. Por otro lado, se ha optimizado el protocolo de dihidroxilación asimétrica aplicado sobre diferentes poliprenoides con el propósito de generalizar esta metodología como paso clave en la síntesis enantioselectiva de epóxidos.

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Author Biographies

Alejandro F. Barrero, University of Granada

Department of Organic Chemistry, Institute of Biotechnology

José F. Quílez del Moral, University of Granada

Department of Organic Chemistry, Institute of Biotechnology

María del Mar Herrador, University of Granada

Department of Organic Chemistry, Institute of Biotechnology

Elena M. Sánchez, University of Granada

Department of Organic Chemistry, Institute of Biotechnology

Jesús F. Arteaga, University of Granada

Department of Organic Chemistry, Institute of Biotechnology

References

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Published

2020-08-05

Issue

Vol. 50 No. 4 (2006): Regular Issue

Section

Regular Articles

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