Abstract Dihydrobenzo [h] coumarins (5a–7a) and their 4??methyl analogs (5b–7b) were synthesized from 1??naphthol via two different synthetic routes. One pathway is the direct condensation of 5, 8??dihydro??1??naphthol (9) with malic acid or ethyl acetoacetate, affording 7, 10??dihydrobenzo [h] coumarins 7a and 7b, respectively. The other is through the oxidation of 7, 8, 9, 10??tetrahydrobenzo [h] coumarins (15a–b), followed by the reduction ...