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 › Research › peer review

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.

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
Externally published	Yes

Keywords

Polyketide
Rearrangements
Selective oxidation
Structure elucidation

ASJC Scopus subject areas

Biochemistry
Drug Discovery
Organic Chemistry

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10.1016/j.tet.2011.05.021

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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.",

keywords = "Polyketide, Rearrangements, Selective oxidation, Structure elucidation",

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.\}",

note = "Funding information: We are grateful to the EPSRC / BBSRC for grant E021611 (A.C.M., J.W. and J.H.) and EPSRC for a studentship (RWS) for funding this work.",

year = "2011",

month = jul,

day = "8",

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

language = "English",

volume = "67",

pages = "5098--5106",

journal = "TETRAHEDRON",

issn = "0040-4020",

publisher = "Elsevier Ltd.",

number = "27-28",

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TY - JOUR

T1 - Mupirocin F

T2 - 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.

N1 - Funding information: We are grateful to the EPSRC / BBSRC for grant E021611 (A.C.M., J.W. and J.H.) and EPSRC for a studentship (RWS) for funding this work.

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.

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.

KW - Polyketide

KW - Rearrangements

KW - Selective oxidation

KW - Structure elucidation

UR - https://www.scopus.com/pages/publications/79958761967

U2 - 10.1016/j.tet.2011.05.021

DO - 10.1016/j.tet.2011.05.021

M3 - Article

AN - SCOPUS:79958761967

SN - 0040-4020

VL - 67

SP - 5098

EP - 5106

JO - TETRAHEDRON

JF - TETRAHEDRON

IS - 27-28

ER -

Mupirocin F: Structure elucidation, synthesis and rearrangements

Abstract

Keywords

ASJC Scopus subject areas

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