Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity
Synthesis of StrophasterolA Guided by a Proposed Biosynthesis and Innate Reactivity
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DOI：
10.1002/anie.201605752
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发表时间：
2016-09-12
影响因子：
16.6
通讯作者：
Heretsch, Philipp
中科院分区：
文献类型：
--
作者：
Heinze, Robert C.;Lentz, Dieter;Heretsch, Philipp
strophasterolA是阿尔茨海默病中内质网（ER）应激的调节剂，也是结构上前所未有的第二甾醇类的第一个成员，通过其提出的生物合成和两次C-H氧化的关键步骤实现了合成。通过对中间体的固有反应性分析，确定了一种制备-氯-羟基-酮烯酮的新方法，以及其葡萄状-酮醇重排为-酮羧酸的新方法。
The synthesis of strophasterolA, a moderator of endoplasmatic reticulum (ER) stress in Alzheimer's disease, and the first member of a structurally unprecedented class of secosterols, was achieved through the implementation of a key step of its proposed biosynthesis and two C-H oxidations. Analysis of the innate reactivity of the intermediates enabled the identification of a novel way to prepare an -chloro--hydroxy--keto enone, as well as its vinylogous -ketol rearrangement to a -keto carboxylic acid.