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Studies On Novel Approach Towards The Total Synthesis Of Agarofuran Sesquiterpenoids

Posted on:2019-12-01Degree:MasterType:Thesis
Country:ChinaCandidate:Y L BoFull Text:PDF
GTID:2404330566976819Subject:Pharmacy
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The agarofuran sesquiterpenoids are an important class of organic heterocyclic compounds.These sesquiterpenoids exhibit a broad spectrum of biological activities and pharmacological effects.The synthesis of agarofuran sesquiterpenoids have attracted considerable attention by scientists because of the unique structure and complex stereochemistry.This thesis aimed at a new strategy for the efficient construction of the agarofuran skeleton,which consists of the following two parts:Chapter 1 summarized the distribution,chemical structure and biological activities of the agarofuran sesquiterpenoids,and reviewed the strategies for the skeleton construction of the agarofuran in the total synthesis of some agarofuran sesquiterpenoids.Charter 2 described our new strategy and exploration for the synthesis of the agarofuran skeleton.Starting from L-(-)carvone,the five-membered ring structure of the hydrindenone derivative 2-15 was efficiently constructed through reductive oxy-Nazarov cyclization which developed in our group previously,then a three-membered ring of the compound 2-19 was synthesized by the Simmons-Smith cyclopropanation,which laid the foundation for the construction of the agarofuran skeleton by the intramolecular ringexpansion cyclization reaction.Figure 1 Retrosynthesis of Agarofuran skeleton...
Keywords/Search Tags:Total synthesis, Sesquiterpenoids, Agarofuran, Reductive oxy-Nazarov cyclization, Simmons-Smith cyclopropanation
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