Synthesis 2012; 44(17): 2779-2785
DOI: 10.1055/s-0032-1316643
paper
© Georg Thieme Verlag Stuttgart · New York

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
› Author Affiliations
Further Information

Publication History

Received: 24 April 2012

Accepted: 13 June 2012

Publication Date:
08 August 2012 (online)


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.

Supporting Information

Primary Data