Neolignans from an Aniba species

Phytochemistry
1975.0

Abstract

A benzene extract of the trunk wood of an Aniba species contained 3a-allyl-2-aryl-.%methoxy-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofurans which may be responsible, through sequential Cope, retro-Claisen and Claisen rearrangements respectively for the formation of the co-occurring 5-allyl-2-aryl-5-methoxy-3-methyl-2,3,5,6-tetrahydro-6-oxobe~ofurans; the 6-O-allyl-2-aryl-5-methoxy-3-methyl-2,3_dihydrobenzofurans and the 7-allyl-2-aryl-6-hydroxy-5-methoxy-3-methyl-2,3-dihydrobenzofurans. The examination of the stereochemistry of these products led to the formulation of burchellin, previously isolated from Aniba burchellii Kostermans, as (2S,3S,3aR)-3a-allyl-5-methoxy-2 piperonyl-3-methyl-2,3,3a,6-tetrahydro-6-oxobenzofuran. The structure 1-allyl-4,8-dihydroxy-7-(3 methoxy-4,5-methylenedioxyphenyl)-6-methyl-3-oxobicyclo[3,2,1]octane is tentatively proposed for an additional neolignan.

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