Regio and stereoselective hydroxylation of a-agarofuran by biotransformation of rhizopus nigricans

• JULIO ALARCÓN ^[1] ; JOEL B ALDERETE ^[2] ; SERGIO AGUILA ^[1] ; MARTIN G PETER ^[3]
  1. [1] Universidad del Bío-Bío

     Universidad del Bío-Bío

     Comuna de Concepción, Chile

     
  2. [2] Universidad de Concepción

     Universidad de Concepción

     Comuna de Concepción, Chile

     
  3. [3] University of Potsdam

     University of Potsdam

     Kreisfreie Stadt Potsdam, Alemania

     

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• Localización: Journal of the Chilean Chemical Society (Boletín de la Sociedad Chilena de Química), ISSN-e 0717-6309, ISSN 0366-1644, Vol. 50, Nº. 4, 2005, págs. 715-718
• Idioma: inglés
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• Resumen

  • A new synthesis of 9a-hydroxy-a-agarofuran (6a) is described, using a microbiological hydroxylation a-agarofuran (5) as the key reaction. The stereochemistry of the biohydroxylation was determined on the basis of a NOESY-experiment and GIAO calculations at the B3LYP/cc-pVDZ level. A strong g-effect was observed at C15 of the agarofuran ring which was correctly predicted by the GIAO-B3LYP calculations