Preparation of (5R)-4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one from (-)-limonene oxide : a novel intermediate to the synthesis of 4-5-5 fused tricarbocyclic core present in terpenic natural products
dc.contributor.author | Pisoni, Diego dos Santos | pt_BR |
dc.contributor.author | Silva, Daniel Borges | pt_BR |
dc.contributor.author | Schenato, Rossana Angelica | pt_BR |
dc.contributor.author | Ceschi, Marco Antonio | pt_BR |
dc.date.accessioned | 2010-07-13T04:18:58Z | pt_BR |
dc.date.issued | 2004 | pt_BR |
dc.identifier.issn | 0103-5053 | pt_BR |
dc.identifier.uri | http://hdl.handle.net/10183/24575 | pt_BR |
dc.description.abstract | Este trabalho refere-se à síntese enantiosseletiva da dienona (5R)-4,8-dimethylbicyclo[3.3.0]oct- 1(8),3-dien-2-one. Este intermediário, pode ser reconhecido como um bloco de construção versátil para a síntese de uma grande variedade de compostos com esqueleto biciclo[3.3.0]octano. A estratégia sintética empregada aqui faz uso da reatividade invertida de um precursor cianoidrina TMS-éter, como equivalente de ânion acila, para promover uma reação de alquilação intramolecular. A síntese formal do (-)-kelsoeno foi realizada pela preparação do intermediário avançado (1R,5S,8R)-4,8- dimethylbicyclo[3.3.0]oct-3-en-2-one, a partir da hidrogenação seletiva do composto intitulado (5R)- 4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one. | pt_BR |
dc.description.abstract | This paper describes the conversion of the readily available (-)-limonene oxide to the new (5R)- 4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one. This compound holds the prospect of serving as a useful chiral building block or intermediate to prepare a variety of compounds having a bicyclo[3.3.0]octane framework. The synthetic strategy made use of the umpolung reactivity of cyanohydrin TMS ether, as an acyl anion equivalent, in order to promote intramolecular alkylation. The formal synthesis of (-)-kelsoene was achieved by preparing a known advanced intermediate (1R,5S,8R)-4,8-dimethylbicyclo[3.3.0]oct-3-en-2-one via selective hydrogenation of the named compound (5R)-4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one. | en |
dc.format.mimetype | application/pdf | |
dc.language.iso | eng | pt_BR |
dc.relation.ispartof | Journal of the Brazilian Chemical Society. São Paulo. Vol. 15, n. 5 (2004), p. 652-657 | pt_BR |
dc.rights | Open Access | en |
dc.subject | Limonene oxide | en |
dc.subject | Sintese enantioseletiva | pt_BR |
dc.subject | Produtos naturais | pt_BR |
dc.subject | Bicyclo[3.3.0]octane | en |
dc.subject | Chiral | en |
dc.subject | Terpenos | pt_BR |
dc.subject | Quirais : Sintese organica | pt_BR |
dc.subject | Building block | en |
dc.title | Preparation of (5R)-4,8-dimethylbicyclo[3.3.0]oct-1(8),3-dien-2-one from (-)-limonene oxide : a novel intermediate to the synthesis of 4-5-5 fused tricarbocyclic core present in terpenic natural products | pt_BR |
dc.type | Artigo de periódico | pt_BR |
dc.identifier.nrb | 000447558 | pt_BR |
dc.type.origin | Nacional | pt_BR |
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