Route2polyTepr · A Unified Route to Polycyclic Terpenes

A Unified Route to Polycyclic Terpenes

Polycyclic terpenes are a very important class of compounds within natural products and drug molecules. Despite their medicinal properties, the complexity of their structures makes them extremely challenging synthetic targets for organic chemists. Currently the access to these molecules is mostly limited to multi-step and tedious preparations. In order to address this problem, we envisaged that xanthate radical precursors can play a strategic role in construction of core structures of polycyclic terpenes. In the first line of research we proposed the use of alpha-ketonyl radicals, derived from xanthates which can be formed from cyclic enones through epoxides. The second line of research involved utilization of subsequent radical and polar reactions (Horner–Wadsworth–Emmons) in order to form difficult polycyclic scaffolds. Our initial plan included the demonstration of the utility of the method by its application to total synthesis of the natural product Maritimol. The first objective of the project was to develop the new synthetic methodology which will allow access to a library of disubsituted enones via radical / polar pathway from easily available starting materials. Products of this reaction can be further transformed into bicyclic and polycylic structures, allowing new and facile approach to a number of medicinally relevant terpenes. The second objective was to carry out the total synthesis of Maritimol.

Текст от CORDIS, на английски · Данни: CORDIS, © Европейски съюз