A Facile approach toward 8-O-4'-neolignans: synthesis of threo-7',8'-dihydromachilin D through Jacobsen epoxidation

Bernal FA, Cuca LE, Fadini L (2015) A Facile approach toward 8-O-4'-neolignans: synthesis of threo-7',8'-dihydromachilin D through Jacobsen epoxidation Revista Facultad de Ciencias Básicas 11(1), 114-129.

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.

Leibniz-HKI-Authors

Freddy Alexander Bernal

Identifier

doi: https://doi.org/10.18359/rfcb.385