Asymmetric Synthesis with Boronic Esters

这项研究是由有机合成化学项目资助的。马特森博士正在开发基于硼原子的新型合成工具。这项技术提供了一种极其强大的方法来控制复杂分子各部分的相对立体化学。它将在制备控制昆虫所需的极其纯净的信息素方面非常有用。基于硼酸酯化学的定向不对称合成已被发现适用于天然产物合成中的各种问题，该项目将扩展我们对硼酸酯化学的基础知识，并将其应用于新类型的合成问题。为了展示和改进该方法已知的特征，将进行几种手性昆虫信息素的合成。这些都带来了重大但现实的合成挑战，这将展示该方法的一些优势，该方法现在理论上能够提供1000：1的粗品手性异构体比。这种方法提供的明确的立体化学和以高纯度形式产生所有立体异构体的能力应该有助于证明未知信息素的构型。将研究新的硼酸酯化学，其目的是将通过这种化学产生的硼酸酯与通过其他方法获得的分子片段连接起来，从而使这种化学更容易地应用于合成高度复杂的天然产物。

This research is being funded by the Organic Synthesis Chemistry Program. Dr. Matteson is developing new synthetic tools based upon the boron atom. This technique provides an extremely powerful way of controlling the relative stereochemistry of parts of a complex molecule. It will be very useful in preparing extremely pure pheromones needed in controlling insects. Directed asymmetric synthesis based on boronic ester chemistry has been found to be applicable to a wide variety of problems in natural product synthesis, and the proposed project will extend our basic knowledge of boronic ester chemistry and extend its applicability to new types of synthetic problems. To demonstrate and refine the features of the method that are already known, synthesisof several chiral insect pheromones will be undertaken. These provide significant but realistic synthetic challenges which will demonstrate some of the advantages of the approach, which is now theoretically capable of providing 1000:1 chiral isomer ratios of crude products The unequivocal stereochemistry and ability to produce all stereoisomers in highly pure form provided by this method should be useful for proving configurations of as yet unknown pheromones. New boronic ester chemistry will be investigated which has as its goal the connection of boronic esters produced via this chemistry with molecular fragments which may be obtained by other means, so that this chemistry can be applied more readily to the synthesis of highly complex natural products.