2-フェノキシメチルクロマノン類縁体の合成と反応 ロテノイドに関する研究(第2報)

抄録

Preparation of 2-phenoxymethylchromone (10 a, b), chromanol (11 a, b) and chromanone (12 a, b) and the attempt to convert to rotenoids were described.
Condensation of ethyl phenoxyacetate (7 a, b) and acetophenone (8) afforded 2-phenoxymethylchromone (10 a, b).
Bromination of the corresponding chromanone (5 a) gave a mixture of mono-bromides (12 a, b) and a dibromide (12 c). Reaction of 12 c with KNH₂ afforded bromochromone (13).
Treatment of chromanol (11 a) with PPA or H₂SO₄ and chromene (14) with HBr-AcOH gave the same bicyclo-3, 9-dioxa-(4, 3, 1)-decane derivative (17 a).
Reaction of chromone alcohol (19) with PPA gave coumaranone derivative (20).
Phenol oxidation reaction of dihydroxyphenoxymethylchromanone (5 b) afforded hydroxymethylchromanone (23 a).