Quassinoids exhibit diverse biological properties and pose synthetically challenging targets. Focusing on accomplishments over the past 15 years, we discuss strategies and tactics of total syntheses as well as SAR and biological functions.

The Cs2CO3/oxone®-mediated C3-alkylation of indoles proceeds in moderate to high yields with a variety of C4–C7 functionalized indoles and is applicable to 2-, 3- and 4-hydroxymethyl pyridines and related electron-deficient heterocycles, permitting novel late-stage drug functionalizations and preparations of dimethyltryptamine analogs. Preliminary mechanistic studies support a chain process starting with an initital oxidation of the alcohol to the corresponding aldehyde, followed by a subsequent condensation onto indole and reduction/ hydride delivery from another equivalent of the primary alcohol.