作者:Fiona J. Black、Philip J. Kocienski
DOI:10.1039/b920285d
日期:——
(4E,8E,10E)-9-Methyl-4,8,10-sphingatrienine, a core component of marine sphingolipids, was synthesised for the first time using a copper(I)-mediated 1,2-metallate rearrangement of a lithiated glycal as a key step. It was converted to phalluside-1, a cerebroside isolated from the ascidian Phallusia fumigate. By an analogous route, (4E,8E)-9-methyl-4,8-sphingadiene was synthesised and converted to Sch II, a cerebroside that induces fruiting body formation in the basidiomycete Schizophyllum commune.
(4E,8E,10E)-9-甲基-4,8,10-斯潘加三烯是一种海洋鞘脂类的核心成分,首次通过铜(I)催化的1,2-金属重排反应合成了锂化的甘蓝作为关键步骤。将其转化为phalluside-1,这是一种从海鞘Phallusia fumigate中分离出的脑苷脂。通过类似的路径,合成了(4E,8E)-9-甲基-4,8-斯潘加二烯,并将其转化为Sch II,这是一种能诱导担子菌Schizophyllum commune形成子实体的脑苷脂。