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dc.contributor.author | Cantin Sanz, Angel | es_ES |
dc.contributor.author | Lull, C. | es_ES |
dc.contributor.author | Primo Millo, Jaime | es_ES |
dc.contributor.author | Miranda Alonso, Miguel Ángel | es_ES |
dc.contributor.author | Primo Yufera, Eduardo | es_ES |
dc.date.accessioned | 2018-02-05T08:38:11Z | |
dc.date.available | 2018-02-05T08:38:11Z | |
dc.date.issued | 2001 | es_ES |
dc.identifier.issn | 0957-4166 | es_ES |
dc.identifier.uri | http://hdl.handle.net/10251/96489 | |
dc.description.abstract | [EN] (-)-(1S,2R,3R,4S)-1,2-Epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate has previously been identified as the active compound of Minthostachys tomentosa responsible for the insecticidal activity against Oncopeltus fasciatus. Its structure was initially assigned on the basis of spectral data. In order to confirm the structure and to define the stereochemistry, stereoselective synthesis of its enantiomer, (+)-(1R,2S,3S,3R)-1,2-epoxy-1-methyl-4-(1-methylethyl)-cyclohex-3-yl acetate, starting from (R)-(-)piperitone, was carried out using a Sharpless reaction as the key step. The natural product is dextro-rotatory while the synthetic product is levo-rotatory. Measurements of insecticidal activities of the different steroisomers revealed that only the natural product is active. | es_ES |
dc.language | Inglés | es_ES |
dc.publisher | Elsevier | es_ES |
dc.relation.ispartof | Tetrahedron Asymmetry | es_ES |
dc.rights | Reserva de todos los derechos | es_ES |
dc.subject.classification | BIOQUIMICA Y BIOLOGIA MOLECULAR | es_ES |
dc.subject.classification | QUIMICA ORGANICA | es_ES |
dc.title | Isolation, structural assignment and insecticidal activity of (1S,2R,3R,4S)1,2-epoxy-1-methyl-4-(1-methyl)cyclohex-3-yl acetate, a natural product from Minthostachys tomentosa | es_ES |
dc.type | Artículo | es_ES |
dc.identifier.doi | 10.1016/S0957-4166(01)00094-5 | es_ES |
dc.rights.accessRights | Abierto | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Instituto Universitario Mixto de Tecnología Química - Institut Universitari Mixt de Tecnologia Química | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Departamento de Biotecnología - Departament de Biotecnologia | es_ES |
dc.contributor.affiliation | Universitat Politècnica de València. Departamento de Química - Departament de Química | es_ES |
dc.description.bibliographicCitation | Cantin Sanz, A.; Lull, C.; Primo Millo, J.; Miranda Alonso, MÁ.; Primo Yufera, E. (2001). Isolation, structural assignment and insecticidal activity of (1S,2R,3R,4S)1,2-epoxy-1-methyl-4-(1-methyl)cyclohex-3-yl acetate, a natural product from Minthostachys tomentosa. Tetrahedron Asymmetry. 12(4):677-683. doi:10.1016/S0957-4166(01)00094-5 | es_ES |
dc.description.accrualMethod | S | es_ES |
dc.relation.publisherversion | https://doi.org/10.1016/S0957-4166(01)00094-5 | es_ES |
dc.description.upvformatpinicio | 677 | es_ES |
dc.description.upvformatpfin | 683 | es_ES |
dc.type.version | info:eu-repo/semantics/publishedVersion | es_ES |
dc.description.volume | 12 | es_ES |
dc.description.issue | 4 | es_ES |
dc.relation.pasarela | S\21313 | es_ES |