Studies on the Michael addition of naphthoquinones to sugar nitro olefins: first synthesis of polyhydroxylated hexahydro-11H-benzo[a]carbazole-5,6-diones and hexahydro-11bH-benzo[b]carbazole-6,11-diones

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dc.contributor.authorOtero, Jose M.
dc.contributor.authorBarcia, Jose C.
dc.contributor.authorSalas, Cristian O.
dc.contributor.authorThomas, Pablo
dc.contributor.authorEstevez, Juan C.
dc.contributor.authorEstevez, Ramon J.
dc.date.accessioned2024-01-10T12:43:07Z
dc.date.available2024-01-10T12:43:07Z
dc.date.issued2012
dc.description.abstractA strategy for the synthesis of the novel (6bR,7R,8S,9S,10S,10aR)-8-(benzyloxy)-7,9,10-trihydroxy-6b,7,8,9,10,10a-hexahydro-11H-benzo[a]carbazole-5,6-dione is reported. The key steps were the Michael addition of 2-hydroxy-1,4-naphthoquinone to 1-nitrocyclohexene or 3-O-benzyl-5,6-dideoxy-1,2-O-isopropylidene-6-nitro-alpha-D-xylo-hex-5-enefuranose and the diastereoselective intramolecular Henry reaction of 3-O-benzyl-5,6-dideoxy-S-C-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-1,2-O-isopropylidene-6-nitro-alpha-D-glucofuranose to give the key (1S,25,35,4R,5R,6R)-3-(benzyloxy)-1,2,4-trihydroxy-5-(3'-hydroxy-1',4'-naphthoquinon-2'-yl)-6-nitrocyclohexane. When 2-hydroxy-1,4-naphthoquinone was replaced by (1,4-dimethoxynaphthalen-2-yl)lithium, the novel (1R,2S,35,4R,4aS,11bS)-2-(benzyloxy)-1,3,4-trihydroxy-1,2,3,4,4a,5-hexahydro-11bH-benzo[b]carbazole-6,11-dione was obtained. (C) 2011 Elsevier Ltd. All rights reserved.
dc.description.funderSpanish Ministry of Science And Innovation
dc.description.funderFPU
dc.description.funderXunta de Galicia
dc.description.funderUniversity of Santiago de Compostela
dc.fechaingreso.objetodigital11-04-2024
dc.format.extent10 páginas
dc.fuente.origenWOS
dc.identifier.doi10.1016/j.tet.2011.11.072
dc.identifier.issn0040-4020
dc.identifier.urihttps://doi.org/10.1016/j.tet.2011.11.072
dc.identifier.urihttps://repositorio.uc.cl/handle/11534/77568
dc.identifier.wosidWOS:000299759000035
dc.information.autorucQuímica;Salas C;S/I;101425
dc.information.autorucQuímica;Thomas P ;S/I;197815
dc.issue.numero5
dc.language.isoen
dc.nota.accesoContenido parcial
dc.pagina.final1621
dc.pagina.inicio1612
dc.publisherPERGAMON-ELSEVIER SCIENCE LTD
dc.revistaTETRAHEDRON
dc.rightsacceso restringido
dc.subjectSugar
dc.subjectQuinones
dc.subjectNitro compounds
dc.subjectMichael addition
dc.subjectHenry reaction
dc.subjectIndoles
dc.subjectHENRY REACTION
dc.subjectEFFICIENT SYNTHESIS
dc.subjectD-GLUCOSE
dc.subjectSTEREOCONTROLLED TRANSFORMATION
dc.subjectANTINEOPLASTIC AGENTS
dc.subjectGENERAL-ROUTE
dc.subjectAMINO ACIDS
dc.subjectNITROSUGARS
dc.subjectDERIVATIVES
dc.subjectFACILE
dc.subject.ods03 Good Health and Well-being
dc.subject.odspa03 Salud y bienestar
dc.titleStudies on the Michael addition of naphthoquinones to sugar nitro olefins: first synthesis of polyhydroxylated hexahydro-11H-benzo[a]carbazole-5,6-diones and hexahydro-11bH-benzo[b]carbazole-6,11-diones
dc.typeartículo
dc.volumen68
sipa.codpersvinculados101425
sipa.codpersvinculados197815
sipa.indexWOS
sipa.indexScopus
sipa.trazabilidadCarga SIPA;09-01-2024
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