síntese e avaliação da atividade fitotóxica de derivados da α-santonina synthesis and evaluation of the phytotoxic activity of α-santonin derivatives
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síntese e avaliação da atividade fitotóxica de derivados da α-santonina synthesis and evaluation of the phytotoxic activity of α-santonin derivatives

;Elson S. Alvarenga;Luiz C. A. Barbosa;William A. Saliba;Francisco F. P. Arantes;Antônio J. Demuner;Antônio A. Silva
greece and rome 2009 Vol. 32 pp. 401-406
173
alvarenga2009qumicasntese

Abstract

Mixtures of α-Santonin and various solvents were irradiated by either high or low pressure mercury lamps. The photochemical reactions afforded lumisantonin (11) (76% in acetonitrile), (3S,3aS,9bS)-3,6,6-trimethyl-3,3a,4,5-tetrahydronafto[1,2-b]furan-2,7(6H,9bH)dione (12) (100% in acetonitrile), 10α-acetoxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (8) (26% in acetic acid), 10α-hydroxy-3-oxo-1,7αH,6,11βH-guaia-4-en-6,12-olide (10) (32%) and (E)-3-((3S,3aS,7aS)-3-methyl-2-oxo-6-(propan-2-ylidene)hexahydrobenzofuran-7-(7aH)-ylidene)propanoic acid (9) (44%) (in water/ acetic acid 1:1, v/v). Lactone 12 was also prepared by irradiation of lumisantonin in diethyl ether. Lactones 8 and 10 were converted, respectively, into the 10α-acetoxy-3β-hydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (13) (87%) and 3β,10α-dihydroxy-1,7αH,6,11βH-guaia-4-en-6,12-olide (14) (75%) by sodium borohydride reduction. The effects of the compounds on the development of radicle of Sorghum bicolor and Cucumis sativus were evaluated.

Keywords

photochemistry

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DOI:
10.1590/S0100-40422009000200025
URL:
http://www.scielo.br/scielo.php?script=sci_arttext...

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