Abstract
A short and versatile synthesis of α,β-dibenzyl-γ-butyrolactones has been developed starting from inexpensive materials by applying Stobbe condensation and following the novel reductive cyclisation with sodiumborohydride. Natural products Suchilactone (5a), Kaerophyllin (5b), savinin (5d) and anhydropodorhizol (5f) were prepared in racemic form. New thionolactones (6a–6e) were prepared by treating these lignans with Lawesson’s reagent. For all the prepared compounds the antioxidant, anti-inflammatory (5-lipoxygenase inhibition) and cytotoxic (Brine shrimp lethality test) activities were tested. The compounds 5a, 5b, 5c, 5d, 5e and 5f showed good 5-lipoxygenase inhibition activity. The thiono lignan 6d showed impressive cytotoxic activity.
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