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Neolignans are natural phenylpropanoid dimers with C-O-C linkages. Currently, neolignans remain as important synthetic targets due to their reported biological potential against parasites and fungal infections. Thereof, a new approach for the synthesis of the 8-O-4'-neolignan 7',8'-dihydromachilin D based on Jacobsen epoxidation as key step is described here. This stereoselective synthesis proceeded in only 4 steps in 3.9% overall yield. Jacobsen epoxidation was firstly optimized regarding to yield and enantioselectivity employing trans-stilbene as model substrate.
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Bernal et al. (2015) studied this question.
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