RT journal article
T1 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
A1 Botubol Ares, José Manuel
A1 Durán Peña, María Jesús
A1 Macías Sánchez, Antonio José
A1 R. Hanson, J.
A1 González Collado, Isidro
A1 Hernández Galán, Rosario
A2 Química Orgánica
AB 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.
PB The Royal Society of Chemistry
YR 2015
FD 2015
LK http://hdl.handle.net/10498/20588
UL http://hdl.handle.net/10498/20588
LA eng
DS Repositorio Institucional de la Universidad de Cádiz
RD 21-sep-2026