Terbium --
Resorcinol(Raney Ni, H2) --> cyclohexanedion-1,3(chloroacetaldehyde, NaHCO3) -->Tetrahydrobenzofyranone (NH3,EtOH, 160°,8hr)--> Tetrahydroindolone
All these steps are not too complicated and give high yield. Difficulties begin with dehydrogenation - reaction with palladium catalist is clean but hard to reproduce. So, another route (bromination to 5 position with CuBr2 and dehidrobromination with Li2CO3) was suggested (Het. 23(1),1985,p.169), but it requires Tosyl- or benzoyl- protection on nitrogen.