Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (-)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents.
Asymmetric Alkylation of Anthrones, Enantioselective Total Synthesis of (-)- and (+)-Viridicatumtoxins B and Analogues Thereof: Absolute Configuration and Potent Antibacterial Agents.
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DOI：
10.1021/jacs.6b12654
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发表时间：
2017-03-15
影响因子：
15
通讯作者：
Shamoo Y
中科院分区：
文献类型：
--
作者：
Nicolaou KC;Liu G;Beabout K;McCurry MD;Shamoo Y
本发明描述了一种使用奎尼丁或奎宁衍生的催化剂的蒽酮与环烯丙基溴的相转移催化不对称烷基化反应。利用温和的碱性条件和低至0.5 mol %的催化剂负载，并实现高达>99：1的dr选择性，该不对称反应成功地应用于对映选择性地产生（-）-和（+）-葡萄球菌毒素B，从而允许分配这种天然存在的抗生素的绝对构型。虽然开发的C10取代的蒽酮的不对称合成预计在有机合成中找到更广泛的应用，但其直接应用于构建各种设计的对映体纯的葡萄球菌毒素B类似物导致发现了该分子的高效但更简单的类似物。这些研究有望促进药物发现和开发新的抗菌剂。
A phase transfer catalyzed asymmetric alkylation of anthrones with cyclic allylic bromides using quinidine- or quinine-derived catalysts is described. Utilizing mild basic conditions and as low as 0.5 mol % catalyst loading, and achieving up to >99:1 dr selectivity, this asymmetric reaction was successfully applied to produce enantioselectively (−)- and (+)-viridicatumtoxins B, and thus allowed assignment of the absolute configuration of this naturally occurring antibiotic. While the developed asymmetric synthesis of C10 substituted anthrones is anticipated to find wider applications in organic synthesis, its immediate application to the construction of a variety of designed enantiopure analogues of viridicatumtoxin B led to the discovery of highly potent, yet simpler analogues of the molecule. These studies are expected to facilitate drug discovery and development efforts toward new antibacterial agents.
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影响因子：
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