Tetrahedron p. 6601 - 6612 (1996)
Update date:2022-08-11
Topics:
Veith, Martin
Dettner, Konrad
Boland, Wilhelm
Larvae of the leaf beetle Phaedon armoraciae produce the iridoids chrysomelidial 1 and plagiodial 3 from geraniol 6 by an oxidative sequence identical to that known in plants. Following ω-oxidation of geraniol the resulting 8-hydroxygeraniol 7 is oxidised via 8-oxogeraniol 14 and 8-hydroxygeranial 15 and to the dialdehyde 8. In plants this transformation is achieved by NADP+ dependent oxidoreductases. However, in the defensive secretion of several leaf beetles an oxygen-dependent oxidase is present. The enzyme catalyses the removal of the C(1)- and C(8)-H(R) hydrogen atoms (Re-specificity) from the diol 7 yielding 8-oxogeranial 8.
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