Asymmetric Synthesis with Boronic Esters

这项研究由有机合成化学项目资助。马特森博士正在开发新的基于硼原子的合成工具。这种技术提供了一种非常有效的方法来控制复杂分子的相对立体化学。这对制备极纯的信息素防治昆虫有重要意义。基于硼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，本课题将扩展我们对硼酯化学的基础知识，并扩展其对新型合成问题的适用性。为了证明和完善已知方法的特征，将进行几种手性昆虫信息素的合成。这些提出了重要但现实的合成挑战，这将证明该方法的一些优点，该方法现在理论上能够提供1000:1的粗产物手性异构体的比例。该方法所提供的明确的立体化学和以高纯度形式生产所有立体异构体的能力，对于证明未知信息素的构型是有用的。新的硼酯化学将被研究，其目标是通过这种化学方法产生的硼酯与可以通过其他方法获得的分子片段的连接，以便这种化学可以更容易地应用于高度复杂的天然产物的合成。

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.