| dc.creator | de Oca, ACBM | |
| dc.creator | Correia, CRD | |
| dc.date | 2003 | |
| dc.date | 2014-11-18T20:37:16Z | |
| dc.date | 2015-11-26T16:58:49Z | |
| dc.date | 2014-11-18T20:37:16Z | |
| dc.date | 2015-11-26T16:58:49Z | |
| dc.date.accessioned | 2018-03-28T23:46:28Z | |
| dc.date.available | 2018-03-28T23:46:28Z | |
| dc.identifier | Arkivoc. Arkat Usa Inc, n. 390, n. 403, 2003. | |
| dc.identifier | 1551-7012 | |
| dc.identifier | WOS:000220556500037 | |
| dc.identifier | http://www.repositorio.unicamp.br/jspui/handle/REPOSIP/74122 | |
| dc.identifier | http://www.repositorio.unicamp.br/handle/REPOSIP/74122 | |
| dc.identifier | http://repositorio.unicamp.br/jspui/handle/REPOSIP/74122 | |
| dc.identifier.uri | http://repositorioslatinoamericanos.uchile.cl/handle/2250/1278030 | |
| dc.description | The novel aryl platynecines 3a/3b were synthesized from endocyclic 4-aryl enecarbamates 8a/8b by a concise and practical route. The synthesis was based on an efficient preparation of 4-aryl enecarbamates 8a/8b from 3-pyrrolines by means of a Heck arylation using aryldiazonium tetrafluoroborates, followed by a highly stereoselective cycloaddition of the 4-aryl enecarbamates 8a/8b to 2-chloroethyl ketene to afford exclusively the 7-endo-(2-chloroethyl) cyclobutanones 12a/12b in good yields (67% and 65%). Baeyer-Villiger oxidation of the cyclobutanones 12a/12b occurred with high regioselectivity to furnish the aza-lactones 13a/13b in 96% and 90% yields. Reduction of lactones 13a and 13b with LiAlH4 gave the desired aryl platynecines 3a/3b. The total synthetic sequence involved 6 steps and provided the aryl platynecines 3a/3b in an overall yield of 41% and 38%, respectively. These compounds are the first examples of necine bases bearing an aromatic substituent on the azabicyclo[3.3.0] octane framework and incorporate some of the key structural element of the pharmacologically active 1,3,4-trisubstituted pyrrolines which act as antagonists of the chemokine receptor CC5. | |
| dc.description | 10 | |
| dc.description | 390 | |
| dc.description | 403 | |
| dc.language | en | |
| dc.publisher | Arkat Usa Inc | |
| dc.publisher | Gainesville | |
| dc.publisher | EUA | |
| dc.relation | Arkivoc | |
| dc.relation | Arkivoc | |
| dc.rights | aberto | |
| dc.source | Web of Science | |
| dc.subject | pyrrolizidines | |
| dc.subject | endocyclic enecarbamates | |
| dc.subject | Heck arylation | |
| dc.subject | aryl pyrrolines | |
| dc.subject | [2+2] cycloaddition | |
| dc.subject | aryl platynecine | |
| dc.subject | Ccr5 Receptor Antagonists | |
| dc.subject | Alkaloids | |
| dc.subject | Functionality | |
| dc.subject | Efficient | |
| dc.subject | Analogs | |
| dc.subject | Hiv | |
| dc.title | Synthesis of aryl pyrrolizidines from endocyclic enecarbamates. Novel applications of the Heck arylation of 3-pyrrolines using diazonium salts | |
| dc.type | Artículos de revistas | |
