New Synthetic Approaches to Halogenated Medium Ring Ethers from Laurencia

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The halogenated medium ring ethers from Laurencia species have attracted much synthetic attention since the isolation of Laurencin in the 1960s.1,2 We have recently proposed and experimental corroborated a unifying biogenesis of these structurally complex molecules.3,4 In that work we employed a novel intramolecular cyclisation protocol. We now intend to extend this work to a more flexible intermolecular functionalization method. In this manner we will target the naturally occurring chlorobromide medium ring ethers of the family.The project fits with at least two EPSRC priority areas: Catalysis & Novel and Efficient Chemical Synthesis.1. Irie, T.; Suzuki, M.; Masamune, T. Tetrahedron Lett. 1965, 16, 1091-1099. 2. For a review see: Wang, B.-G.; Gloer, J. B.; Ji, N.-Y.; Zhao, J.-C. Chem. Rev. 2013, 113, 3632-36853. Bonney, K. J.; Braddock, D. C. J. Org. Chem. 2012, 77, 9574-9584 and references cited therein. For more recent work targeting bicyclic members of the class see: Braddock, D. C.; Sbircea, D.-T. Chem. Commun. 2014, 50, 12691-12693.4. For the development of the method see: Bonney, K. J.; Braddock, D. C.; White, A. J. P.; Yaqoob, M. J. Org. Chem. 2011, 76, 97-104.