利用 1,2-金属重排合成菌核侧耳素-1 和 Sch II。

Synthesis of phalluside-1 and Sch II using 1,2-metallate rearrangements.

机构信息

School of Chemistry and Institute of Process Research and Development, Leeds University, Leeds, LS2 9JT, UK.

出版信息

Org Biomol Chem. 2010 Mar 7;8(5):1188-93. doi: 10.1039/b920285d. Epub 2010 Jan 14.

DOI:10.1039/b920285d

PMID:20165812

Abstract

(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.

摘要

(4E,8E,10E)-9-甲基-4,8,10-二十碳三烯碱，一种海洋神经鞘脂类的核心成分，首次通过铜（I）介导的锂化糖醛 1,2-金属重排反应合成，该反应是关键步骤。它被转化为来源于 Phallusia fumigate 的神经节苷脂 1。通过类似的途径，（4E,8E）-9-甲基-4,8-二十碳二烯碱被合成，并转化为 Sch II，一种在担子菌 Schizophyllum commune 中诱导子实体形成的神经节苷脂。