New Synthetic Approaches to Halogenated Medium Ring Ethers from Laurencia

Lead Research Organisation: Imperial College London
Department Name: Dept of Chemistry

Abstract

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.

Publications

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Studentship Projects

Project Reference Relationship Related To Start End Student Name
EP/N509486/1 01/10/2016 31/03/2022
1804928 Studentship EP/N509486/1 01/10/2016 30/09/2019 Yusrah Al-Gharebawi
 
Description We have successfully developed an intermolecular functionalisation method to construct the key stereochemical features of the target compounds.
Exploitation Route The results of this research will be published in due course. They will be of benefit to researchers in the area and to the broader organic chemistry community as previously unrecognised methodology.
Sectors Chemicals,Education,Pharmaceuticals and Medical Biotechnology