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dc.contributor.authorBotubol Ares, José Manuel
dc.contributor.authorDurán-Peña, María Jesús
dc.contributor.authorMacías Sánchez, Antonio José
dc.contributor.authorR. Hanson, J.
dc.contributor.authorGonzález Collado, Isidro
dc.contributor.authorHernández Galán, Rosario
dc.contributor.otherQuímica Orgánicaen_US
dc.date.accessioned2018-06-05T12:23:56Z
dc.date.available2018-06-05T12:23:56Z
dc.date.issued2015
dc.identifier.urihttp://hdl.handle.net/10498/20588
dc.description.abstractThe 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.en_US
dc.formatapplication/pdfen_US
dc.language.isoengen_US
dc.publisherThe Royal Society of Chemistryen_US
dc.rightsAttribution-NonCommercial-NoDerivatives 4.0 Internacional*
dc.rightsinfo:eu-repo/semantics/openAccess
dc.rights.urihttp://creativecommons.org/licenses/by-nc-nd/4.0/*
dc.sourceOrganic & Biomolecular Chemistry, 2015, 13, 465en_US
dc.titleThe synthesis of 3-hydroxy-2,4,8-trimethyldec- 8-enolides and an approach to 3,4-dihydroxy- 2,4,6,8-tetramethyldec-8-enolideen_US
dc.typeinfo:eu-repo/semantics/articleen_US
dc.rights.accessRightsinfo:eu-repo/semantics/openAccessen_US
dc.identifier.doi10.1039/c4ob01792g


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Attribution-NonCommercial-NoDerivatives 4.0 Internacional
This work is under a Creative Commons License Attribution-NonCommercial-NoDerivatives 4.0 Internacional