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*, Philip J. Kocieński*, Arndt W. Schmidt, Thomas N. Snaddon, Colin A. Kilner
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Publication History

Received: 24 April 2012

Accepted: 13 June 2012

Publication Date:
08 August 2012 (eFirst)

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.

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