Polyfunctional bicyclo[6.3.0]undecane intermediates

Abstract
On thermolysis, 2-hydroxy-1-isopropyl-2-vinylbicyclo[4.3.0]non-6-en-8-one 18 undergoes oxy-Cope rearrangement followed by an ‘ene’ reaction to give 5-hydroxy-11-isopropyl-8-methyltricyclo[6.3.0.01,5]undec-10-ene-9-one 21, which is cleaved by Pb(OAc)4–I2 to 11-isopropyl-8-methylbicyclo[6.3.0]undeca-1,10-diene-5,9-dione 23. Aspects of the chemistry of the dione are explored.

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