Abstract
Treatment of ethyl 10-oxo-2-(trimethylsilylmethyl)undeca-2,8-dienoate with a Lewis acid or fluoride afforded ethyl2-[2-(2-oxopropyl)cyclohex-1-yl]acrylate and/or7-acetyl-9-methylenebiocyclo-[4.3.0]nonan-8-one. Under these conditions the 2 Z,8 E- and 2 Z,8 Z-precursors give predominantly cis-disubstituted six-membered ring products, while the 2 E,8 E- and 2 E-8 Z-precursors give primarily trans-disubstituted six-membered ring products.
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