5. Biomimetic Total Synthesis of Polyether Ionophores.

Biomimetic polyepoxide Æ polyether cyclisation cascades are being investigated in the context of the total synthesis of the complex polyether antibiotic, etheromycin. An advanced etheromycin intermediate containing the ABCD rings has been prepared by the directed cyclisation of a keto diepoxide. This work underlines the power and utility of directed polyepoxide cyclisations in rapidly constructing the characteristic tetrahydrofuran and tetrahydropyran ring systems contained in polyether ionophores, accompanied by a high level of regio- and stereocontrol. Useful new methods for acyclic stereocontrol and asymmetric synthesis are also being developed as an integral part of this project.

cylisation cascade in synthesis of etheromycin

Selected publications

  1. Paterson, I.; Tillyer, R. D.; Smaill, J. B. Studies in biomimetic polyether synthesis: construction of an ABCD-ring subunit of etheromycin using polyepoxide cascade cyclisations. Tetrahedron Lett. 1993, 34, 7137.
  2. Paterson, I.; Tillyer, R. D.; Ryan, G. R. Studies in biomimetic polyether synthesis: synthesis of an A-ring subunit of etheromycin. Tetrahedron Lett. 1993, 34, 4389.
  3. Paterson, I.; Craw, P. A. Studies in polyether synthesis: controlled bisepoxide cyclisation using a β-diketone group. Tetrahedron Lett. 1989, 30, 5799.
  4. Paterson, I.; Boddy, I.; Mason, I. Studies in polyether synthesis using polyepoxide cyclisations. Tetrahedron Lett. 1987, 28, 5205.

Current Projects

  1. Synthesis of Bioactive Marine Metabolides.
  2. New Methods for the Synthesis of Polyketide Natural Products.
  3. Expanding Polyketide Diversity.
  4. New Reagents for Asymmetric Aldol Reactions.
  5. Biomimetic Total Synthesis of Polyether Ionophores.
  6. Designed Synthesis of Lophotoxin Analogues.
  7. Designed Synthesis of Novel Macrolide Antibiotics Related to Erythromycin.
  8. Transition State Modelling of Reactions (with Dr J. M. Goodman and Prof C. Gennari)