Flash presentation 89 Lauroxanes are a series of nonterpenoid C15-metabolites derived from fatty acid metabolism (acetogenins), that have been isolated from the Laurencia species of red algae. These compounds exhibit a wide range of biological activity including antitumor, antimicrobial, antifeedant and pesticide activity. They possess a halogenated carbon backbone and a cyclic ether 5- to 9-membered rings. For this formal synthesis of (¿)-isolaurepinnacin and (+)-rogioloxepane A, we applied a methodology recently developed in our group. The strategy is based in two key steps: intermolecular Nicholas reaction (interNR) using ß-hydroxy-¿-lactones as the nucleophile and a ring closing metathesis (RCM).

We thank the Spanish MECD CEI10/00018 and MINECO, cofinanced by the European Regional Development Fund (ERDF), CTQ2011-28417-C02-01 and CTQ2011- 22653, and IMBRAIN project (FP7-REGPOT-2012-CT2012-31637-IMBRAIN), funded under the 7th Framework Programme (CAPACITIES), by financial support. JRL thanks MINECO for a FPI fellowship.

Trabajo presentado en la XXV Reunión Bienal de Química Orgánica celebrada en Alicante del 4 al 6 de junio de 2014.

Peer Reviewed