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Of. Merrilactone A Semi-synthetic

Posted on:2010-06-12Degree:MasterType:Thesis
Country:ChinaCandidate:W GengFull Text:PDF
GTID:2191360272494765Subject:Clinical pharmacy
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Merrilactone A,which was isolated from Illicium merrillianum in 2000,has been shown to possess neurotrophic activity in cultures of fetal rat cortical neurons and therefore is expected to hold therapeutic potential in the treatment of neurodegeneration associated with Alzheimer's and Parkinson's diseases.But the content is very scarce,so synthesis is particularly important.The total synthesis of foreign routes are already quite mature,but the semisynthesis part has not been researched.When exploring the toxicity of the composition which is extracted from the poisonous plants of Illiciaceae,a number of non-volatile,and peculiar skeleton sesquiterpene components have been found,such as seco-prezizaane class and category anislactone.They are commonly found in Illiciaceae,and most in the form of lactone,the existence of these components are the root cause of neurotoxicity of Illiciaceae. Pseudoanisatin,6-deoxypseudoanisatin and cycloparviflorolide can be isolated from Star Anise whose structures are like merrilactone A,so we consider to use the semi-synthetic method to transform these compounds to our aim product through chemical reactions.We have designed five synthetic path and conducted a preliminary exploration.We hope to hold the five membered ring and use different methods to open the rest of the ring re-condensation to form the skeleton structure of Merrilactone A,followed by further side-chain transformation.The main experiment to explore different methods of open-loop,including the hydrolysis,alcoholysis, oxidation,reduction respectively.Among them,the alcohol solution and the product of oxidation to be more desirable,so as to lay the foundation for the next transformation.
Keywords/Search Tags:Semi-synthetic, Merrilactone A, pseudoanisatin, 6-deoxypseudoanisatin, cycloparviflorolide, Transesterification, Oxidation, deoxidation
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