Practical synthesis of 9-substituted triptycene derivatives

A series of 9-position substituted triptycene derivatives were synthesized from 9-substituted anthracenes. Diels–Alder reaction was the key reaction to form the scaffold; both benzoquinon and aryne were studied as dienophile. The diastereomers of triptycene 10a were separated by chiral high-performance liquid chromatography (HPLC) column.