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Molecules 2009, 14(1), 160-173; doi:10.3390/molecules14010160
Article

Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin

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Received: 26 November 2008 / Revised: 9 December 2008 / Accepted: 31 December 2008 / Published: 1 January 2009
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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, the most active compounds were oxabicycles possessing a carbonyl group conjugated with a double bond.
Keywords: Helminthosporic acid; Helminthosporol; Helminthosporal; Helminthosporins oxabicycle; Herbicide; [4+3] Cycloaddition; Oxyallyl cation; Phytogrowth properties Helminthosporic acid; Helminthosporol; Helminthosporal; Helminthosporins oxabicycle; Herbicide; [4+3] Cycloaddition; Oxyallyl cation; Phytogrowth properties
This is an open access article distributed under the Creative Commons Attribution License which permits unrestricted use, distribution, and reproduction in any medium, provided the original work is properly cited.

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Barbosa, L.C.A.; Nogueira, L.B.; Álvares Maltha, C.R.; Teixeira, R.R.; Silva, A.A. Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin. Molecules 2009, 14, 160-173.

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