New Synthetic Route to Butanolide Lignans by a Ruthenium Complex Catalyzed Hydrogenation of the Corresponding Stobbe's Fulgenic Acids

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Abstract
A new two-step total synthesis of butanolide lignans (or dibenzylbutyrolactine lignans) is described, which affords the title compounds in good yield and with a very short work-up time. It involves a ruthenium carbonyl hydrtidr complex-catalyzed hydrogensation of the corresponding dibenzylidene sucicnic acids (fulgenic acids). Since the catalytic hydrogenation (second step) is a total yielding process, the overall yield determining step is the preparation of the fulginic acid intermediates by the Stobbe condensation (first step), which has consequently been revised to improve many details. This simple process moreover allows hexadeuterated butanolide lignans to be readily obtained for isotopic dilution mass spectral measurements. The syntheses of a selection of lignans, namely enterolactone, matairesinol, hinokinin, dimethylmatairesinol and cordigerine, are described to illustrate the whole procedure.
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