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Stereselective Synthesis of 4-Hydroxy-8,12-Guaianolides from Santonin

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Stereselective Synthesis of 4-Hydroxy-8,12-Guaianolides from Santonin

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Nombre: Blay;Bargues;Cardona ...
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dc.contributor.author Blay, Gonzalo es_ES
dc.contributor.author Bargues, Victoria es_ES
dc.contributor.author Cardona, Luz es_ES
dc.contributor.author Collado, Ana M. es_ES
dc.contributor.author García, Begoña es_ES
dc.contributor.author Muñoz Roca, María Del Carmen es_ES
dc.contributor.author Pedro, Jose R. es_ES
dc.date.accessioned 2020-10-16T05:59:33Z
dc.date.available 2020-10-16T05:59:33Z
dc.date.issued 2000-04-07 es_ES
dc.identifier.issn 0022-3263 es_ES
dc.identifier.uri http://hdl.handle.net/10251/152174
dc.description.abstract [EN] Hydroxyester 2, easily obtained from santonin (1), has been transformed into 10¿-hydroxyguai-3-en-8,12-olide 6, a good intermediate for the synthesis of natural 8,12-guaianolides. Compound 6 was obtained from 2 by photochemical rearrangement of its acetyl derivative 7, stereoselective hydrogenation on Pd/C, reduction, regioselective elimination, hydrolysis, and lactonization. The synthesis of the natural guaianolides 3¿5 was carried out in two sequences in which the regioselective elimination of a hydroxyl group at C10 with triflic anhydride or SOCl2 to afford, respectively, the endo or exo double bond on C10 and the regioselective opening of the C3¿C4 ¿-epoxide were the key steps. es_ES
dc.description.sponsorship Financial support from the European Commission (Grant FAIR CT96-1781) and from the Dirección General de Investigación Científica y Técnica (DGICYT; Grant PB 94-0985) is gratefully acknowledged. V.B. and A.M.C. are especially thankful to the Conselleria de Cultura, Educació i Ciencia (Generalitat Valenciana), and European Commission, respectively, for a grant. es_ES
dc.language Inglés es_ES
dc.publisher American Chemical Society es_ES
dc.relation.ispartof The Journal of Organic Chemistry es_ES
dc.rights Reserva de todos los derechos es_ES
dc.subject.classification FISICA APLICADA es_ES
dc.title Stereselective Synthesis of 4-Hydroxy-8,12-Guaianolides from Santonin es_ES
dc.type Artículo es_ES
dc.identifier.doi 10.1021/jo991756n es_ES
dc.relation.projectID info:eu-repo/grantAgreement/EC/FP4/FAIR961781/EU/TERPENES AS NATURAL CHIRAL STARTING MATERIAL FOR THE SYNTHESIS OF FLAVOURS, FRAGRANCES, PHARMACEUTICALS AND BIOCONTROLE AGENTS/ es_ES
dc.relation.projectID info:eu-repo/grantAgreement/MEC//PB94-0985/ es_ES
dc.rights.accessRights Cerrado es_ES
dc.contributor.affiliation Universitat Politècnica de València. Departamento de Física Aplicada - Departament de Física Aplicada es_ES
dc.description.bibliographicCitation Blay, G.; Bargues, V.; Cardona, L.; Collado, AM.; García, B.; Muñoz Roca, MDC.; Pedro, JR. (2000). Stereselective Synthesis of 4-Hydroxy-8,12-Guaianolides from Santonin. The Journal of Organic Chemistry. 65(7):2138-2144. https://doi.org/10.1021/jo991756n es_ES
dc.description.accrualMethod S es_ES
dc.relation.publisherversion https://doi.org/10.1021/jo991756n es_ES
dc.description.upvformatpinicio 2138 es_ES
dc.description.upvformatpfin 2144 es_ES
dc.type.version info:eu-repo/semantics/publishedVersion es_ES
dc.description.volume 65 es_ES
dc.description.issue 7 es_ES
dc.identifier.pmid 10774038 es_ES
dc.relation.pasarela S\17449 es_ES
dc.contributor.funder European Commission es_ES
dc.contributor.funder Generalitat Valenciana es_ES
dc.contributor.funder Ministerio de Educación y Ciencia es_ES


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