Abstract An account of the total synthesis of (±)-,(+)-heliespirone A and (±)-,(−)-heliespirone C is presented. In the first-generation total synthesis, we found rac-24a could be easily transformed to rac-heliespirones A & C in a biomimic way. Taking the disappointing diastereoselectivity of prenylation from 3 to 4, the nonselective dihydroxylation from 4 to 5 and the lenthy route in strategy A into account, we designed a different synthetic plan ...