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Study on Synthesis of Key Intermediate7,7-disubsituted Norbornane Derivative of Natural Product Ocophyllals A

Author: ZhouWei
Tutor: XiaWuJiong
School: Harbin Institute of Technology
Course: Biomedical Engineering
Keywords: 2-arly benzofurans Ocophyllas A key intermediate 7-benzoylnorboranederivative
CLC: O626.11
Type: Master's thesis
Year: 2012
Downloads: 4
Quote: 0
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Abstract


2-Arly benzofuran compounds, with good anti-tumor activity, antifungal activity,antioxidant activity and antiviral activity, are potential leading compounds in medicinalchemistry. Developing a novel synthetic method of constructing this structure has beena weighty thing for medicinal chemists, because of its variety of drug activity, rich typeof compounds and scarce natural sources. However, the traditional way to construct theABF structure, key intermediate, has confined the chemists to synthesize the new ABFcompounds found in nature efficiently. Founding a novel key intermediate has beenincreasingly important.Dihydrofurans has been synthesized by7-benzoylnorbornane derivatives via anovel retro-Claisen photorearrangement. This enlighten us a novel routine to constructthe2-arly benzofuran compounds. However, how to introdue the7-benzoylnorboranestructure is very important issue because we can efficiently synthesize the2-arlybenzofuran derivatives via this methods, especially the natural compounds.In this essay, we disicuss the introduction of the key intermediate of the naturalcompounds Ocophyllas A.We designed the key intermediate of natural compoundsOcophyllas A. Use and compared the Wagner-Meerwein rearrangement,metal-templated oxidative cycloadditions,5-subsituted cyclopentadiene Diels-Aldercycloadditon and5,5-subsituted cyclopentadiene Diels-Alder cycloaddtion inconsructing7-benzoylnorborane deravatives. At the end, we selected the best routineand successfully synthesized the5,5-subsituted cyclopentadiene compounds. Wediscussed its chemical property and applied it into7-benzoylnorborane deravatives’synthesis. Although the4enantiomers has arouse during the reaction and we can hardlyseparate them, this result can also give us much idea for the further work for this keyintermediate.

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CLC: > Mathematical sciences and chemical > Chemistry > Organic Chemistry > Heterocyclic compounds > Five heterocycles containing a single different atoms > Oxa -mao ( furans) family
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