Synthesis of oxocanes. Iron(III) salts Catalyzed a Prins-1,5-Hydride Shift-oxidation Tandem Reaction

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.In the last years, the presence of green and sustainable chemistry in organic synthesis community has increased significantly. lron is one of the most important sustainable metal catalysts in organic chemistry because is biological relevant, environmentally friendly, can adopt different oxidation states, and it is one of the most abundant and inexpensive in the earth 's crust. [1] In this work, we use iron(ll I) salts to catalyze a tandem readion of three chemical events; Prins readion, 1,5-hydride shift and the final oxidation. The resulting 1,7-hydroxy ketones are known precursors far eight membered ring oxacycles synthesis (Scheme 1). [2] With suitable substituents we can obtain natural products derivatives like cis-lauthisan in few steps and soft conditions.We thank the Spanish MINECO, co-financed by the European Regional Development Fund (ERDF), CTQ2014-56362-C2-1-P for financia! support. J. M. L. S. thanks Canary Government (ACllSI) far a Predoctoral fellowship.Peer Reviewe