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Paper | Regular issue | Vol 27, No. 9, 1988, pp.2185-2196
Published online, 1st January, 1970
DOI: 10.3987/COM-88-4321
New Synthetic Route to Butanolide Lignans by a Ruthenium Complex Catalyzed Hydrogenation of the Corresponding Stobbe‘s Fulgenic Acids

Massimo Bambagiotti-Alberti,* Silvia A. Coran, Franco F. Vinvieri, Nadia Mulinacci, and Giuseppe M. L. Pieraccini

*Dipartimento di Scienze Farmaceutiche, Università di Firenze, Via Gino Capponi 9, I-50121 Firenze, Italy

Abstract

A new two-step total synthesis of butanolide lignans (or dibenzylbutyrolactone lignans) is described, which affords the title compounds in good yield and with a very short work-up time. It involves a ,ruthenium carbonyl hydride complex-catalyzed hydrogenation of the corresponding dibenzylidene succinic acids (fulgenic acids). Since the catalytic hydrogenation (second step) is a total yielding Process, the overall yield determining step is the preparation of the fulgenic 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, hinoknin, dimethylmatairesinol and cordigerine, are described to illustrate the whole procedure.