An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane-2,6-dione

Fredrik Almqvist Department of Organic Chemistry, Umeå University, S-901 87, Umeå, Sweden

Lars Eklund Department of Organic Chemistry, Umeå University, S-901 87, Umeå, Sweden

Torbjöm Frejd Department of Organic Chemistry, Umeå University, S-901 87, Umeå, Sweden

Abstract

Conjugate addition of Meldrum's acid to 2-cyclohexenone followed by direct cyclization in PPA/acetic acid constitutes a shorter, more reproducible and higher yielding route to bicyclo[2.2.2]octane-2,6-dione than previous methods. The crude dione could be used as substrate for the baker's yeast reduction to (1R, 4S, 6S)-bicyclo[2.2.2]octane-6-ol-2-one.

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An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane-2,6-dione

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An Improved Procedure for the Synthesis of Bicyclo[2.2.2]octane-2,6-dione

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