Solution (source code)

= Solution

A route from the supplied cyclohexenone starts with \b[conjugate methyl addition]. Form an <organocuprate> from methylmagnesium bromide and Cu(I), or use catalytic Cu(I) with controlled methylmagnesium addition, to obtain 3-methylcyclohexanone after <protonation>. <copper> directs 1,4 rather than direct 1,2 addition, so the <ketone> remains intact.

Generate its less hindered <kinetic enolate> at the alpha <carbon> \b[opposite the methyl-bearing side], using LDA at low temperature, and trap with phenylselenyl chloride. <oxidation> of the resulting alpha-selenyl <ketone> with <hydrogen> peroxide produces a selenoxide, whose syn elimination introduces the enone double bond on that side. Renumbering the double bond from the <carbonyl> gives \b[5-methylcyclohex-2-en-1-one A]. The selenium-containing phenyl group is a removable reagent fragment, not a <carbon> building block incorporated into A; the only new product <carbon> is the allowed methyl group. Regioselective kinetic <enolization> is important: enolizing the other alpha site would regenerate an enone with the methyl in the wrong position. This route produces racemic A unless a separate asymmetric step is introduced, which is sufficient for the stereochemically unspecified starting <ketone>.