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

doi:10.1016/j.tet.2011.05.021

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 journal › Article (Academic Journal) › peer-review

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 language	English
Pages (from-to)	5098-5106
Number of pages	9
Journal	Tetrahedron
Volume	67
Issue number	27-28
DOIs	https://doi.org/10.1016/j.tet.2011.05.021
Publication status	Published - 8 Jul 2011

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STRUCTURAL AND MECHANISTIC STUDIES OF TYPE II POLYKETIDE SYNTHASES AND RELATED?
Simpson, T. J.
1/02/04 → 1/06/07
Project: Research

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title = "Mupirocin F: structure elucidation, synthesis and rearrangements",

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.",

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

year = "2011",

month = jul,

day = "8",

doi = "10.1016/j.tet.2011.05.021",

language = "English",

volume = "67",

pages = "5098--5106",

journal = "Tetrahedron",

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TY - JOUR

T1 - Mupirocin F: structure elucidation, synthesis and rearrangements

AU - Scott, Robert W.

AU - Murphy, Annabel C.

AU - Wu, Ji'en

AU - Hothersall, Joanne

AU - Cox, Russell J.

AU - Simpson, Thomas J.

AU - Thomas, Christopher M.

AU - Willis, Christine L.

PY - 2011/7/8

Y1 - 2011/7/8

N2 - 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.

AB - 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.

U2 - 10.1016/j.tet.2011.05.021

DO - 10.1016/j.tet.2011.05.021

M3 - Article (Academic Journal)

VL - 67

SP - 5098

EP - 5106

JO - Tetrahedron

JF - Tetrahedron

SN - 0040-4020

IS - 27-28

ER -

Mupirocin F: structure elucidation, synthesis and rearrangements

Abstract

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STRUCTURAL AND MECHANISTIC STUDIES OF TYPE II POLYKETIDE SYNTHASES AND RELATED?

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