[Zurück]

S. Hecko, M.D. Mihovilovic:
"Development of synthetic strategies towards neolignans";
Vortrag: 7th Paul Ehrlich MedChem EuroPhD Network Symposium, Vienna; 25.08.2017 - 27.08.2017.

Lignans and their subclass neolignans belong to a large class of predominantly plant derived natural products originating from oxidative coupling of two C6C3 units. These secondary metabolites are known to act on an ecological level in plant-plant or plant-insect interactions and were shown to have additional protective properties in response to stress conditions like trauma, infections or exposure to UV radiation. [1] The structures typically coupled by a β,β´-linkage between two C6C3 units are termed lignans, whereas neolignans are composed of any other connection between these sub-units. Among these structures especially those bearing a 8,1'-linkage with an additional 2',7-epoxy bridge giving benzofurane-core units were shown to have interesting biological activities. Kadsurenone as being one of the prominent examples displays potent PAF (platelet-activating factor) agonism that was proven to indirectly interfere with LPS induced TNF-α production.

The assembly of substituted benzofurane core units has been studied by Engler et al. forming the target structures that are derived from two phenylpropanoid fragments in a Lewis acid assisted formal [2+5]-cycloaddition.

For the decoration of these desired key fragments several approaches were examined, devising a modular strategy by stepwise assembly of the designated structures.

Total Synthesis, Medicinal Chemistry, Neolignans