Morphine and its derivatives continue to challenge the creativity of synthetic chemists. The aim of this research is to execute a short chiral synthesis of the morphinan system. Chirality is introduced via asymmetric reduction; the key step is the formation of four rings- the tetracyclic phenanthrofuran by an intramolecular Diels-Alder cycloaddition. The fifth ring was completed by three different methods, and three different pentahydrophenanthrofuran systems were obtained.

Morphine and its derivatives continue to challenge the creativity of synthetic chemists. The aim of this research is to execute a short chiral synthesis of the morphinan system. Chirality is introduced via asymmetric reduction; the key step is the formation of four rings- the tetracyclic phenanthrofuran by an intramolecular Diels-Alder cycloaddition. The fifth ring was completed by three different methods, and three different pentahydrophenanthrofuran systems were obtained.