A Facile approach toward 8-O-4'-neolignans: synthesis of threo-7',8'-dihydromachilin D through Jacobsen epoxidation
Abstract
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.
Involved units
Leibniz-HKI-Authors
Identifier
doi: https://doi.org/10.18359/rfcb.385