Sustainable Catalysis: Direct Synthesis of 2,7-Disubstituted Oxepenes

Trabajo presentado en la XXVI Reunión Bienal de Química Orgánica de la Real Sociedad Española de Química, celebrada en Punta Umbría, Huelva (España) del 14 al 17 de junio de 2016.Medium size oxacycles are structural motifs presented in a wide range of marine natural products. [1] Unsaturated seven member oxacycles (oxepenes) represent a main goal due to their biological relevance, as well as, synthetic target. Oxepenes have been synthesized using different methodologies but none of them through dired Prins cyclization. [2] In this work, we obtain 2,7-disubstituted oxepenes in one step with good diastereomeric ratio through dired Prins cyclization with Fe(lll) salts as a sustainable metal catalyst. This methodology is the key step in our approach to the total synthesis of (1) and (2).We thank the Spanish MINECO, co-financed by the European Regional Development Fund (ERDF), CTQ2014-56362-C2-1-P for financial support. D. A. C. thanks MINECO for a FPI fellowship.Peer Reviewe