A Synthesis of the Pseudopterosin A–F Aglycone

John P. Cooksey; Philip J. Kocieński; Arndt W. Schmidt; Thomas N. Snaddon; Colin A. Kilner

doi:10.1055/s-0032-1316643

Synthesis, Table of Contents

Synthesis 2012; 44(17): 2779-2785
DOI: 10.1055/s-0032-1316643

paper

A Synthesis of the Pseudopterosin A–F Aglycone

John P. Cooksey*

School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK, Fax: +44(113)3436401 Email: p.j.kocienski@leeds.ac.uk Email: j.p.cooksey@leeds.ac.uk

,

Philip J. Kocieński*

School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK, Fax: +44(113)3436401 Email: p.j.kocienski@leeds.ac.uk Email: j.p.cooksey@leeds.ac.uk

,

Arndt W. Schmidt

School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK, Fax: +44(113)3436401 Email: p.j.kocienski@leeds.ac.uk Email: j.p.cooksey@leeds.ac.uk

,

Thomas N. Snaddon

School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK, Fax: +44(113)3436401 Email: p.j.kocienski@leeds.ac.uk Email: j.p.cooksey@leeds.ac.uk

,

Colin A. Kilner

School of Chemistry and Institute of Process Research and Development, University of Leeds, Leeds LS2 9JT, UK, Fax: +44(113)3436401 Email: p.j.kocienski@leeds.ac.uk Email: j.p.cooksey@leeds.ac.uk

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Abstract

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Abstract

The synthesis of the pseudopterosin A–F aglycone from 3-methylcatechol features (a) the use of asymmetric Ireland–Claisen and aryl Claisen rearrangements to install three of the four stereocentres present in the molecule and (b) an A→AB→ABC annulation strategy using ring-closing metathesis and cationic cyclisation reactions as the key steps.

Key words

total synthesis - terpenoids - ring closure - rearrangement - metathesis - pericyclic reaction

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References

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