Research On Boron Ate-complex Oxidative Ring Rearrangement Reaction Methodology

Organic boron compound play a very important role in the field of organic chemistry and are widely used in the fields of organic synthesis,materials science,and life and health.Therefore,organic boron compound has a huge social demand and always been a research hotspot.Containing a cyclobutane skeleton are widely distributed in Natural product.many of these natural molecules have strong anti-cancer,anti-virus and other physiological activities.Because of many of them limited by content of nature or the extraction process and other factors,it cannot meet the market demand.Although there have been many reports on cyclobutane synthesis methodologies,the construction of natural molecules containing poly-substituted cyclobutanes,complex cages,and bridged ring and ring systems remains a challenge for chemists.Therefore,it is of great significance to develop practical cyclobutane skeletons and complex natural product molecular scaffold construction methods.Organic boron compounds are a very common type of chemical materials.They have the advantages of simple and readily available materials,operation convenience,stable,and a wide range of applications.They have long been favored by organic chemists.The boron ate-complex 1,2 sigma migration reaction is a known and mature reaction and it is widely used in the synthesis of various organic compounds,Our group the first time proposed intramolecular carbonyl group or ester groupring contract rearrangement reaction constructed cyclobutane and Isotwistane core of the lycopodium alkaloids Palhinine A by boron ate-complex.First,by using benzophenone and 4-pentenyl,4-pentenoic acid benzyl ester boron ate-complex oxidation reaction of Contraction Rearrangement Study,I found that the carbon-boron bond is more easily oxidized and opened than the α-position of the carbonyl group,while the ester substrate is undergoing hydrolysis reactions.In order to avoid the above side reaction,we adjusted the substrate and installed a leaving group in theα-position of the carbonyl group of the precursor before made cyclo-boron ate-complex,We unexpectedly obtained a product containing a furan ring.After being screened by water,oxygen,etc.,the product was unaltered.and also conducted a mechanism and confirming it.We applied this methodology first synthesis of2-benzoyl-furan and not previously relevant literature reported.At the same time,we also design synthesis the core skeleton of Palhinine A using boron ate-complex rearranggement.and obtained key intermediates.In the research,we constructed the structures furan ring by boron ate-complex rearrangement reaction.The reaction mechanism is still under study.