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Synthesis 2002(13): 1857-1866
DOI: 10.1055/s-2002-33919
DOI: 10.1055/s-2002-33919
PAPER
© Georg Thieme Verlag Stuttgart · New York
Synthesis of a Diels-Alder Precursor for the Elisabethin A Skeleton
Further Information
Received
25 April 2002
Publication Date:
09 September 2002 (online)
Publication History
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
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