New Synthetic Approaches to Halogenated Medium Ring Ethers from Laurencia

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, 3632-3685
3. 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.