Highly diastereoselective approach toward (plusmn)-tetraponerine T6 and analogues via the double cycloisomerization-reduction of bis-alkynylpyrimidines

A new, short, and efficient approach toward tricyclic alkaloids, involving the double cycloisomerization-reduction of bis-alkynylpyrimidines, is developed. A highly selective hydrogenation/reduction of the resulting bis-pyrrolopyrimidine allowed for the short, efficient, and highly diastereoselective total synthesis of (plusmn)-tetraponerine T6 and its analogues.