The chemistry of fungi. Part 74. Synthesis of (±)-5-butyl-6,8-dihydroxy-3-pentyl-3,4-dihydroisocoumarin

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Abstract
The title compound (1; R1= Bun, R2= H), which corresponds to the (+)-dihydro-derivative of fusamarin (2), a metabolite of an unidentified species of Fusarium, has been synthesised. (2-Butyl-3,5-dimethoxyphenyl)acetic acid (3; R1= OH, R2= Bun) was obtained from ethyl 3,5-dimethoxyphenylacetate by way of the corresponding 2-formyl derivative (3; R1= OEt, R2= CHO). Reaction of the acid chloride (3; R1= Cl, R2= Bun) with pentylmagnesium bromide furnished 1-(2-butyl-3,5-dimethoxyphenyl)heptan-2-one (4; Ru = Bun), which was reduced to the alcohol (5; R1= H, R2= Bun). Formylation of the acetate (5; R1= Ac, R2= Bun), followed by oxidation and hydrolysis of the ester residue, gave (±)-5-butyl-3-pentyl-6,8-dimethoxy-3,4-dihydroisocoumarin (1; R1= Bun, R2= Me), which was demethylated to (1; R1= Bun, R2= H). In model experiments (±)-6,8-dihydroxy-3-pentyl-3,4-dihydroisocoumarin (1; R1= R2= H) and related derivatives, together with associated isochromans of type (7), have been synthesised.

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