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UBC Theses and Dissertations

Synthesis of potential intermediates in the biosynthesis of flavoglaucin Avelino, Norman G.


Previous work on the biosynthesis of compounds derived by the acyl-polymalonate route is discussed. Flavoglaucin(84), a pigment produced by Aspergillus glaucus, is derived by the acyl-polymalonate route. Feeding experiments using labelled acetate and malonate on flavoglaucin (84), have proven its origin as being from this route, however, no feeding experiments using potential intermediates have been reported. Thus, the initial objective of our research was to synthesize deuterium-labelled compounds which could be regarded as probable intermediates in the biosynthetic route. Subsequent incorporation experiments using cultures of A. glaucus could then provide information which would assist in the elucidation of the biosynthetic sequence leading to flavoglaucin(84). 6-n-heptyl-∝-[deuterio]-2-hydroxybenzaldehyde(92a) and its corresponding acid(92b) are potential intermediates in the biosynthesis of flavoglaucin. Compound(92a) was synthesized from furan(157) and dimethylace-tylene dicarboxylate(158) in eleven steps. Various attempts to synthesize the corresponding acid (92b) from N,N-diethyl-6-n-heptyl-2-methoxybenzairu.de (97), 3-n-hexyl-7-methoxyphthalide (109) , and methyl-6-n-heptyl-∝-[oxo]-2-methoxybenzoate(133) were unsuccessful. The syntheses of 6-n-heptyl-∝-[deuterio]-2-benzyloxybenzaldehyde (165) and 6-n-heptyl-∝-[deuterio]-2-methoxybenzaldehyde were successful but various attempts using several different oxidizing agents failed to oxidize either aldehyde to their corresponding acids.

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