Mupirocin F: structure elucidation, synthesis and rearrangements

Robert W. Scott, Annabel C. Murphy, Ji'en Wu, Joanne Hothersall, Russell J. Cox, Thomas J. Simpson, Christopher M. Thomas, Christine L. Willis

Research output: Contribution to journalArticle (Academic Journal)

7 Citations (Scopus)

Abstract

The structures of two novel metabolites, mupirocins F and F2, from extracts of the mupF mutant of Pseudomonas fluorescens were elucidated by spectroscopic methods. Methyl mupirocin F was synthesised from the triol methyl pseudomonate A by selective oxidation of the 7-hydroxyl group thus firmly establishing the structure of the natural product. Rearrangement of the densely functionalised skeleton led to unusual bicyclic and tricyclic products. (C) 2011 Elsevier Ltd. All rights reserved.

Original languageEnglish
Pages (from-to)5098-5106
Number of pages9
JournalTetrahedron
Volume67
Issue number27-28
DOIs
Publication statusPublished - 8 Jul 2011

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Scott, R. W., Murphy, A. C., Wu, J., Hothersall, J., Cox, R. J., Simpson, T. J., Thomas, C. M., & Willis, C. L. (2011). Mupirocin F: structure elucidation, synthesis and rearrangements. Tetrahedron, 67(27-28), 5098-5106. https://doi.org/10.1016/j.tet.2011.05.021