An expedient route to the pentacyclic core of the tryptoquivaline alkaloids and the total synthesis of natural product (+)-3'-(4-oxoquinazolin-3-yl)spiro[1H-indole-3,5'-oxolane]-2,2'-dione (1) have been achieved. The route is enabled by a key, highly stereoselective, aldol reaction catalysed by a Ag(i) and cinchona-derived aminophosphine ligand system, forming a highly substituted oxazoline ring, and setting the C1 spirocyclic stereocentre for downstream manipulation.
