Several naturally occurring compounds were subjected to late-stage tert-alkylation (Figure ). Initially, the compounds tested performed poorly due to low solubility in DCE at 50 °C. However, useful yields resulted by changing the solvent to chlorobenzene and heating to 100 °C. Thymol and sesamol are adamantylated to produce functionalized 12 and 13 in 38% and 65% yields, respectively. The relatively more complex molecule, estrone, undergoes tert-butylation in 40% yield (14a) and adamantylation in 19% yield (14d).