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Studies On The Construction Of Bicycle[3.n.1]skeletons Based On Alkynones

Posted on:2017-05-18Degree:MasterType:Thesis
Country:ChinaCandidate:Q H ZhangFull Text:PDF
GTID:2271330503968883Subject:Organic Chemistry
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Alkynones are important precusors in various organic syntheses of heterocyclic derivatives. The alkynyl and ketone carbonyl groups in the molecule can influence each other, which leads to the diversity and uniqueness of the reactions of alkynones. Bicyclo[3.n.1]alkanones are skeletons of many natural products and drug molecules. In modern organic chemistry, the synthesis of the bicyclic compounds has become one of the key research interests of chemists. Based on the studies of alkynone compounds in our group and the current research background of bicyclo[3.n.1]alkanones, we carried out a systematic studies on the construction of bicycle[3.n.1]skeletons via alkynones.This thesis is mainly divided into the following two parts:1): Studies on the construction of bicycle[3.n.1]skeletons based on the cyclic alkynonesIn this chapter, we developed a highly efficient and practical AgN Tf2/TfO H synergistically catalyzed cyclization of alkynones to access the bicycle[3.n.1]alkanones(n = 2,3,4,5,9). The reaction condition is mild and convenient, and the products are diversified. The synthetic method in this chapter is not only suitable for different types of substrates, but also could be used in the modification of natural products, such as methyl dihydrojasmonate, ɑ,β-thujone, and 5α-cholestan-3-one. It may provide a new and efficient method for the construction of complex molecules.2): Studies on the construction of cyclohexenone skeletons based on the chain alkynonesCyclohexenone skeleton widely existed in some natural products with special activity. They have simple structure and high reactivity, and are important materials and intermediates in organic synthesis. As an extension of the cyclic alkynones system, we have designed and synthesized series of chain alkynones as substrates, which then could be converted to cyclohexenone skeletons efficiently under the catalysis of TfOH.
Keywords/Search Tags:Alkynone, Bicycle[3.n.1]skeleton, Cyclohexenone skeleton
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