The thia-analog of ambrettolide, 1,8-oxathiacyclohexadecan-2-one (3), was synthesized from â-caprolactone (4). Cleavage of 4 with trimethylsilyl iodide in the presence of ethanol provided iodoester 5, that was converted to the thioether 6 by treatment with tetramethylthiourea and the monoalkoxide of 1,8-octanediol. Collaud cyclization furnished the target compound 3 that contrary to thiocyclopentadecanolides 7, 8 and 9 possesses an intense musk odor.
氮杂物质的
丙酯,1,8-氧
硫环己十六酮(3),是由β-
己内酯(4)合成的。在
乙醇的存在下,使用三甲基
氟化
碘对4进行裂解,得到了
碘酯5,随后通过与四甲基
硫脲和
1,8-辛二醇的单烷氧基化合物反应,将其转化为
硫醚6。Collaud环化反应合成了目标化合物3,与
硫环
十五烷醇酯7、8和9不同,它具有浓烈的
麝香气味。