Synthesis of some 3-arylisochromene, 3-arylisoquinoline, 6H-5-oxachrysene, and benzo[c]phenanthridine analogs of some naturally occurring alkaloids

A 2-benzopyrylium perchlorate 6 was prepared from the keto ester 5. Reduction of 6 followed by dilute HCl affords 6H-5-oxachrysene 10. Reaction of 6 with ammonia solution gives the isoquinoline acid 13. By a short series of steps 13 is cyclized to the dihydrobenzo[c]phenanthridine 16.