Stereoselective Synthesis of Ketals using Thiourea-Based Catalysts

描述（由申请人提供）：本研究的目的是开发更有效和选择性的天然产物或其他含有立体酮或动物结构的药用相关化合物的途径。这项工作可能影响到几个不同的医学领域，包括抗癌、抗菌、抗真菌和抗病毒治疗。该方案的关键技术平台是与硫脲的阴离子结合催化。这为催化SN1取代反应提供了一种以前无法实现的表面控制方法。由于缺乏使用任何类型的催化剂控制来获取碳正离子的方法，这将对各种化学产生深远的影响。阴离子结合催化将主要应用于通过o -糖基化合成螺旋酮/螺旋胺和糖的对映选择性和非对映选择性。这些部分目前很难用高水平的立体控制来制备。

DESCRIPTION (provided by applicant): The purpose of this research is to develop more efficient and selective routes to natural products or other medicinally relevant compounds containing stereogenic ketal or aminal structures. This work may affect several diverse areas of medicine including anticancer, antibacterial, antifungal, and antiviral therapeutics. The key technology platform this proposal builds on is anion binding catalysis with thioureas. This provides a method to catalyze SN1 substitution reactions with previously unattainable facial control. Given the lack of methods to access carbocations with any sort of catalyst control, this should have far-reaching impact on a variety of chemistries. Anion binding catalysis will primarily be applied to the enantioselective and diastereoselective synthesis of spiroketals/spiroaminals and sugars through O-glycosylation. These moieties are currently difficult to prepare with high levels of stereocontrol. PUBLIC HEALTH RELEVANCE: The purpose of this research is to develop new chemical reactions that can provide chemists with more efficient means to prepare potential drugs. This work may affect several diverse areas of medicine including anticancer, antibacterial, antifungal, and antiviral therapeutics.