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Synthesis 2002(13): 1857-1866
DOI: 10.1055/s-2002-33919
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© Georg Thieme Verlag Stuttgart · New York

Synthesis of a Diels-Alder Precursor for the Elisabethin A Skeleton

Thilo J. Heckrodt, Johann Mulzer*
Institut für Organische Chemie der Universität Wien, Währingerstr. 38, 1090 Wien, Austria
Fax: +43(1)427752189; e-Mail: johann.mulzer@univie.ac.at;
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Publication History

Received 25 April 2002
Publication Date:
09 September 2002 (online)

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Abstract

A synthesis of a precursor 2 for the Elisabethin A skeleton is reported. Containing a masked quinone and a (E,Z)-diene subunit, it has the required elements for the envisaged intramolecular Diels-Alder reaction to form the tricyclic system of Elisabethin A. Starting from methylresorcinol, the sequence involves the preparation of an arylacetic acid, which was α-alkylated by a chiral building block. Subsequent HWE reaction and cis-selective Wittig olefination furnished the diene with the desired geometry.

Key words

total synthesis - natural products - alkylations - Wittig reactions - stereoselectivity