synthesis and phytogrowth properties of oxabicyclic analogues related to helminthosporin合成和phytogrowth helminthosporin oxabicyclic类似物相关的属性.pdfVIP

Molecules 2009, 14, 160-173; doi:10.3390/molecule OPEN ACCESS molecules ISSN 1420-3049 /journal/molecules Article Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin Luiz Cláudio Almeida Barbosa 1,*, Leonardo Brandão Nogueira 1, Célia Regina Álvares 1 1 2 Maltha , Róbson Ricardo Teixeira and Antônio Alberto Silva 1 Department of Chemistry, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil; E-mail: leonardolbn@.br (L-B. N.); teixeir5@.br (R-R. T.); crmaltha@ufv.br (C-A. M.) 2 Plant Science Department, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil; E-mail: aasilva@ufv.br (A-A. S.) * Author to whom correspondence should be addressed; E-mail: lcab@ufv.br. Received: 26 November 2008; in revised form: 9 December 2008 / Accepted: 31 December 2008 / Published: 1 January 2009 Abstract: This investigation describes the synthesis and biological evaluation of a series of oxabicyclic analogues related to the helminthosporins. Four oxabicycles were prepared by [4+3] cycloaddition of an oxyallyl carbocation, generated in situ from 2,4-dibromopentan- 3-one, with selected furans. Functional group manipulations of the oxabicyclic architecture generated nine further derivatives. The phytotoxic properties of these oxabicycles were evaluated as their ability to interfere with the growth of Sorghum bicolor and Cucumis sativus seedlings. In both species,