@misc{10498/20588,
year = {2015},
url = {http://hdl.handle.net/10498/20588},
abstract = {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.},
publisher = {The Royal Society of Chemistry},
title = {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},
doi = {10.1039/c4ob01792g},
author = {Botubol Ares, José Manuel and Durán Peña, María Jesús and Macías Sánchez, Antonio José and R. Hanson, J. and González Collado, Isidro and Hernández Galán, Rosario},
}