Regio- and Stereospecific Uncatalyzed Reactions of Electron-Rich Arenes and Olefins at Organomolybdenum Enantiomeric Scaffolds

A novel uncatalyzed reaction between TpMo(CO)2(5-trifluoroacetoxy-η3-5,6-dihydropyranyl/dihydropyridinyl) complexes and electron-rich arenes/olefins is reported. The reaction proceeds under mild reaction conditions so that a variety of functional groups are tolerated. Combined with a stereospecific annulative demetalation, the new reaction provides a rapid access to polycyclic alkaloid structures. The sequential protocol was used to prepare analogues of the antimalarial agent isofebrifugine.