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
dc.creator | Otero, Jose M. | |
dc.creator | Barcia, Jose C. | |
dc.creator | Salas, Cristian O. | |
dc.creator | Thomas, Pablo | |
dc.creator | Estevez, Juan C. | |
dc.creator | Estevez, Ramon J. | |
dc.date.accessioned | 2024-01-10T12:43:07Z | |
dc.date.accessioned | 2024-05-02T16:16:16Z | |
dc.date.available | 2024-01-10T12:43:07Z | |
dc.date.available | 2024-05-02T16:16:16Z | |
dc.date.created | 2024-01-10T12:43:07Z | |
dc.date.issued | 2012 | |
dc.identifier | 10.1016/j.tet.2011.11.072 | |
dc.identifier | 0040-4020 | |
dc.identifier | https://doi.org/10.1016/j.tet.2011.11.072 | |
dc.identifier | https://repositorio.uc.cl/handle/11534/77568 | |
dc.identifier | WOS:000299759000035 | |
dc.identifier.uri | https://repositorioslatinoamericanos.uchile.cl/handle/2250/9265981 | |
dc.description.abstract | A 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.language | en | |
dc.publisher | PERGAMON-ELSEVIER SCIENCE LTD | |
dc.rights | acceso restringido | |
dc.subject | Sugar | |
dc.subject | Quinones | |
dc.subject | Nitro compounds | |
dc.subject | Michael addition | |
dc.subject | Henry reaction | |
dc.subject | Indoles | |
dc.subject | HENRY REACTION | |
dc.subject | EFFICIENT SYNTHESIS | |
dc.subject | D-GLUCOSE | |
dc.subject | STEREOCONTROLLED TRANSFORMATION | |
dc.subject | ANTINEOPLASTIC AGENTS | |
dc.subject | GENERAL-ROUTE | |
dc.subject | AMINO ACIDS | |
dc.subject | NITROSUGARS | |
dc.subject | DERIVATIVES | |
dc.subject | FACILE | |
dc.title | 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 | |
dc.type | artículo |