Structure-Based Organic Synthesis of a Tricyclic N-Malayamycin Analogue

The solid-state structure of crystalline malayamycin A reveals a urea substituent that bisects the plane of the chairlike tetrahydropyran subunit. On the basis of this topological feature, we synthesized a tricyclic N-nucleoside analogue in which an ethano bridge linked the urea NH group with the ring junction of the bicyclic tetrahydrofuropyran unit.