Furan derivatives have been synthesized from 7hydroxy-4-methoxy-2,3-dihydroinden-l -one (7b), -5-met hoxy -1,2,3,4-tetra hydronap ht halen -1 -one 4hydroxy-1methoxy -6,7,8,9tetrahydro-5H-benzocyclohepten-5-one (8b), 6-hydroxy-2a,3-di hydro-2H-naphtho [ 1,8-bc]furan-5(4H) -one (9b), 7-hydroxy-2,3,3a,4-tetrahydronaphtho[l,8-bc]pyran-6(5H) -one (lob), and 7hydroxy-2,2a,3,4-tetrahydrocyclohepta[cd] benzofuran-6( 5 H ) -one (1 1 b). Hydroxy ketones such as (4b), (8b), (lob), and (11 b) which have a strong intramolecular hydrogen bond between the hydroxy and the carbonyl groups easily produced the furan derivatives (l), ( 13), (15), and (16). However, the hydroxy ketones (7b) and (9b) in which the intramolecular hydrogen bond was weak failed to give the furan derivatives ( 12) and ( 14).
8hydroxy