Stereoselective Syntheses of Lignin Model Compounds of the beta-0-4 and beta-1 Types.

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Abstract
The preparation of erythro forms of lignin model compounds of the .beta.-0-4 type by hydroboration of .alpha.-aryloxycinnamic acids, using a borane dimethyl sulfide complex as a reagent, was studied. The erythro form of 1-(4-hydroxy-3-methoxyphenyl)-2-(2-methoxyphenoxy)-1,3-propanediol was obtained in a yield of .apprx. 50%. Acid-catalyzed rearrangements of chalcone oxides result in the formation of .alpha.-formyldesoxibenzoins which give 1,2-diaryl-1,3-propanediols on borohydride reduction. The synthesis of the erythro forms of 1,2-bis(4-hydroxy-3-methoxyphenyl)-1,3-propanediol and 1,2-bis(4-hydroxy-3,5-dimethoxyphenyl)-1,3-propanediol by this reaction route is described; both 1,2-diaryl-1,3-propanediols represent lignin model compounds for the .beta.-1 type of structure.

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