三价铋催化的 Friedel-Crafts 环化反应和立体控制的有机催化方法合成（-）-platensimycin。
A bismuth(III)-catalyzed Friedel-Crafts cyclization and stereocontrolled organocatalytic approach to (-)-platensimycin.
机构信息
Department of Chemistry, Faculty of Science, and Medicinal Chemistry Program of the Life Sciences Institute, National University of Singapore, 3 Science Drive 3, Singapore 117543, Singapore.
出版信息
Org Lett. 2010 Dec 3;12(23):5510-3. doi: 10.1021/ol102390t. Epub 2010 Oct 29.
A high yielding route to the (-)-platensimycin core is communicated. This entailed the discovery of Bi(OTf)(3) to catalyze a Friedel-Crafts cyclization of a free lactol, supplemented by LiClO(4) to suppress the Lewis basicity of the sulfonate group. After TBAF-promoted cyclodearomatization, a diastereoselective conjugate reduction of a dienone was achieved by adopting amine-based organocatalytic rationales to reverse the inherent steric control of the substrate.
我们介绍了一种高产率合成(-)-platensimycin 核心结构的路线。该路线的关键步骤包括发现三氟甲磺酸铋（Bi(OTf)(3)）能够催化游离内脂的傅克环化反应，并用 LiClO(4)抑制磺酸酯基的路易斯碱性。经过三氟化硼四丁基醚促进的环脱氢芳构化反应后，采用基于胺的有机催化原理，实现了一个二烯酮的非对映选择性共轭还原反应，从而逆转了底物固有的立体控制。
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