The preparation of a 10-membered ring macrolactone by selective ozonolysis and the role of the dihydropyran-substituent on the MCPBA-oxidation reaction profile of beta-lapachone phenazines

Journal of the Brazilian Chemical Society

Raphael S. F. Silva²  Tiago T. Guimarães²  Daniel V. Teixeira²  Ana Paula G. Lobato²  Maria Do Carmo F. R. Pinto²  Carlos Alberto De Simone¹  Janaína G. Soares¹  Alessandra G. Cioletti¹  Marilia O. F. Goulart¹  Antonio V. Pinto² 

[1] ,Universidade Federal do Rio de Janeiro Centro de Ciências da Saúde Núcleo de Pesquisas de Produtos NaturaisRio de Janeiro RJ ,Brazil

关键词: beta-lapachone;    ozonolysis;    10-membered ring macrolide;    selectivity;    effect of substituent;   

DOI  :  10.1590/S0103-50532005000600027

来源: SciELO

【 摘 要 】

The benzophenazine from beta-lapachone was submitted to ozonolysis under conditions that selectively furnished the corresponding rigid macrocyclic lactone 7,7-dimethyl-7,8,9,10-tetrahydro-5H-benzo[3,4]oxecino[5,6-b]quinoxaline-5,10-dione in an yield of 52%. The effect of substituents located at the dihydropyrane moiety of the phenazines, namely C2'-OH, C2'-Br and C2'-I, in the oxidation with MCPBA, was also investigated.

【 授权许可】

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