Bicyclo[3,2,1]octanoid,neolignans from Aniba simulans |
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Authors: | Marden A. De Alvarenga Oscar Castro C. Astréa M. Giesbrecht Otto R. Gottlieb |
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Affiliation: | Instituto de Química, Universidade de São Paulo, c.p. 20780, São Paulo, Brasil |
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Abstract: | Six bicyclo[3,2,1]octanoid neolignans, isolated from the benzene extract of Aniba simulans Allen (Lauraceae) trunk wood, are shown to derive from two basic structures: 1-allyl-8-hydroxy-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-7-methyl-3-oxobicyclo[3,2,1]octane, substituted by 4-hydroxy, 4-hydroxy-5-methoxy, 4-methoxy or 4,5-dimethoxy groups; and 1-allyl-8-hydroxy-6-(3′-methoxy-4′,5′-methylenedioxyphenyl)-7-methyl-4-oxobicyclo[3,2,1]oct-2-ene, substituted by 3-hydroxy or 3-hydroxy-5-methoxy groups. The structural proposals are based on spectral data, interconversions synthesis of a derivative from the known (2R,3S,3aS)-3a-allyl-5-methoxy-2-(3′-methoxy,4′,5′-methylenedioxyphenyl)-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofuran. |
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Keywords: | Lauraceae benzofuranoid neolignans bicyclo[3,2,1]octanoid neolignans, benzofuranoid/bicyclo[3,2,1]octanoid interconversion. |
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