三环型可待因类似物的合成

SYNTHESIS OF TRICYCLIC CODEINE ANALOGUE

以愈创木酚为原料,用甲氧甲醚作为芳环上邻锂化反应的定位基,高选择性地生成芳基取代的环已烯醇,经氧化、还原、重排、环合等反应,立体专一性地合成了六氢双苯骈呋喃结构的可待因类似物,总收率为19％。

Guaiacol is protected by the formation of methoxymethyl ether, which results in a regeospecificlithiation when n-BuLi is used. From the produced 1-(2'-methoxy-2'-methoxymethyl-phenyl)-2-cyclohexen-1-ol, the codeine analogue with structure of hexahydrodibenzofuran is obtained by oxida-tion, reduction rearrangement and cyclization, the total yield is 19%.