Diastered and Regiochemical Control in the Functionalization of the Allylic [dbnd] of a Natural 5-(1-Alkenyl)-2-Enono-1,5-Lactone

Sandra R. Signorella Institute de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Corrso 991, 2000, Rosario, Argentina

Raquel M. Cravero Institute de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Corrso 991, 2000, Rosario, Argentina

Luis E. Sala Institute de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Corrso 991, 2000, Rosario, Argentina

Edmundo A. Rúveda Institute de Química Orgánica de Síntesis (CONICET-UNR), Facultad de Ciencias Bioquímicas y Farmacéuticas, Casilla de Corrso 991, 2000, Rosario, Argentina

Abstract

The diastereo and regioselectivity of the bromohydrination of argentilactona [(5R)-(-)-δ-lactone of 5-hydroxydodeca-Z, Z-2,6-dienoic acid] and the regioselectivity of the aqueous acidic opening of its 65,75 and 6R,7R-epoxides were studied. Although the reactions occurred with low diasterofacial control, the regioselectivity observed in all cases was high, suggesting that the sequences could be of some synthetic value.

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Diastered and Regiochemical Control in the Functionalization of the Allylic [dbnd] of a Natural 5-(1-Alkenyl)-2-Enono-1,5-Lactone

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Diastered and Regiochemical Control in the Functionalization of the Allylic [dbnd] of a Natural 5-(1-Alkenyl)-2-Enono-1,5-Lactone

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