Iron(III) catalyzed synthesis of D4 2,7-disubstituted oxepenes

Trabajo presentado en el 11th Spanish-Italian Symposium on Organic Chemistry SISOC-XI celebrado en San Sebastián (España), del 13 al 15 de julio de 2016.Medium size oxacycles are structural motifs present in a wide range of marine natural products. Unsaturated seven member oxacycles (oxepenes) represent a main goal due to their biological relevance, as well as important synthetic targets. Oxepenes have been synthesized using different methodologies but none of them through direct Prins cyclization. In this work, we will present the syntheses of 2,7-disubstituted oxepenes in one step, with good diastereomeric ratio, through direct Prins cyclization with Fe(III) salts as a sustainable metal catalyst. This methodology is the key step in our approach to the total synthesis of (1) and (2) (Scheme 1).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