硫醇-烯烃共氧化方法在1,2,4-三氧杂环己烷药效基团新合成中的应用。
Application of thiol-olefin co-oxygenation methodology to a new synthesis of the 1,2,4-trioxane pharmacophore.
作者信息
O'Neill Paul M, Mukhtar Amira, Ward Stephen A, Bickley Jamie F, Davies Jill, Bachi Mario D, Stocks Paul A
机构信息
Department of Chemistry, University of Liverpool, P.O. Box 147, Liverpool L69 3BX, UK.
出版信息
Org Lett. 2004 Sep 2;6(18):3035-8. doi: 10.1021/ol0492142.
[reaction: see text] Thiol-olefin co-oxygenation (TOCO) of substituted allylic alcohols generates alpha-hydroxyperoxides that can be condensed in situ with various ketones to afford a series of functionalized 1,2,4-trioxanes in good yields. Manipulation of the phenylsulfenyl group in 4a allows for convenient modification to the spiro-trioxane substituents, and we describe, for the first time, the preparation of a new class of antimalarial prodrug.
[反应：见正文] 取代烯丙醇的硫醇-烯烃共氧化反应（TOCO）生成α-羟基过氧化物，该过氧化物可与各种酮原位缩合，以良好的产率得到一系列功能化的1,2,4-三氧杂环己烷。对4a中苯亚磺酰基的操作便于对螺三氧杂环己烷取代基进行修饰，并且我们首次描述了一类新型抗疟前药的制备。
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