Synthesis of (+)-Compactin

Significance

Compactin inhibits HMG-CoA reductase, the rate-controlling enzyme in choles­terol biosynthesis. The synthesis of an advanced intermediate diol J towards the synthesis of (+)-Compactin features MacMillan’s organocatalytic Mukaiyama-Michael reaction to introduce the first stereocenter which then controls the formation of the remaining three chiral centers.