Please use this identifier to cite or link to this item: http://repositorio.unicamp.br/jspui/handle/REPOSIP/102395
Type: Artigo de periódico
Title: Synthesis Of Aryl Pyrrolizidines From Endocyclic Enecarbamates. Novelapplications Of The Heck Arylation Of 3-pyrrolines Using Diazonium Salts
Author: Montes De Oca A.C.B.
Correia C.R.D.
Abstract: 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.
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Rights: fechado
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Address: http://www.scopus.com/inward/record.url?eid=2-s2.0-3242686903&partnerID=40&md5=525232cf1c011fff333b8de073252204
Date Issue: 2003
Appears in Collections:Unicamp - Artigos e Outros Documentos

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