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

Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin

Luiz Cláudio Almeida Barbosa 1,* email, Leonardo Brandão Nogueira 1 email, Célia Regina Álvares Maltha 1 email, Róbson Ricardo Teixeira 1 email and Antônio Alberto Silva 2 email
1 Department of Chemistry, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil 2 Science Department, Federal University of Viçosa, 36570-000, Viçosa, Minas Gerais, Brazil
* Author to whom correspondence should be addressed.
Received: 26 November 2008; in revised form: 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

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MDPI and ACS Style

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.

AMA Style

Barbosa LCA, Nogueira LB, Álvares Maltha CR, Teixeira RR, Silva AA. Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin. Molecules. 2009; 14(1):160-173.

Chicago/Turabian Style

Barbosa, Luiz Cláudio Almeida; Nogueira, Leonardo Brandão; Álvares Maltha, Célia Regina; Teixeira, Róbson Ricardo; Silva, Antônio Alberto. 2009. "Synthesis and Phytogrowth Properties of Oxabicyclic Analogues Related to Helminthosporin." Molecules 14, no. 1: 160-173.

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