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Synthesis 2003(7): 1071-1078
DOI: 10.1055/s-2003-39174
PAPER
© Georg Thieme Verlag Stuttgart ˙ New York

A Versatile Synthesis of Bicyclo[2.2.2]octan-2-one Derivatives

Philip Schmoldt, Jochen Mattay*
Organische Chemie I, Fakultät für Chemie, Universität Bielefeld, Postfach 100131, 33501 Bielefeld, Germany
Fax: +49(521)1066417; e-Mail: mattay@uni-bielefeld.de;
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Publication History

Received 19 November 2002
Publication Date:
09 May 2003 (online)

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Abstract

A novel sequence for the synthesis of substituted bicyclo[2.2.2]oct-5-en-2-one derivatives starting from substituted cyclohex-2-en-1-ones is presented. The Michael addition of malonic esters to an α,β-unsaturated ketone and an intramolecular aldol reaction are the key steps. A generally applicable synthetic strategy for the construction of 5-substituted cyclohex-2-en-1-ones is presented as well.

Key words

bicyclo[2.2.2]octan-2-ones - Michael additions - bicyclic compounds - substituted cyclohex-2-en-1-ones - intramolecular aldol reactions