%0 Journal Article 
%A Botubol Ares, José Manuel
%A Durán Peña, María Jesús
%A Macías Sánchez, Antonio José
%A R. Hanson, J.
%A González Collado, Isidro
%A Hernández Galán, Rosario
%T The synthesis of 3-hydroxy-2,4,8-trimethyldec- 8-enolides and an approach to 3,4-dihydroxy- 2,4,6,8-tetramethyldec-8-enolide
%D 2015
%U http://hdl.handle.net/10498/20588
%X The synthesis of several derivatives of 3-hydroxy-2,4,8-trimethyldec-8-enolide and attempts at the synthesis of 3,4-dihydroxy-2,4,6,8-tetramethyldec-8-enolide (1), a structure which has been assigned to a metabolite of the phytopathogenic fungus, Botrytis cinerea, gave products whose spectroscopic data had significant differences from those reported for the natural product 1. The rare 11-membered lactone rings were constructed by ring-closing metathesis reactions. The increase in conformational restrictions imposed by the substituents has a high influence on the stereochemistry of the ring-closing metathesis reaction and gives rise to a decrease in the yield for the synthesis of 11-membered lactones. The predominant alkene which was obtained was the (Z)-isomer. The observed spectroscopic differences between the synthesized lactones and the natural product and the spectroscopic data of its acetylated derivative 26a allowed us to revise the structure 1 to that of the γ-butyrolactone 26.
%~ Universidad de Cádiz