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Synthesis Studies Of Daphlongamine E

Posted on:2017-09-22Degree:MasterType:Thesis
Country:ChinaCandidate:X K YangFull Text:PDF
GTID:2311330503961581Subject:Chemistry
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Daphlongamine E is one of Calyciphylline Aalkaloids which was isolated from from the leaves of Daphniphyllum longeracemosum by professor Hao in 2009, it contains five-membered fused rings skeleton and six quaternary carbon center. Owing to its complex structure, the total synthesis of Daphlongamine E is proved to be very challenging.In this dissertation, a novel synthesis for five membered skeleton of Daphlongamine E was reported in 12 steps starting from the known compound 2-29 and 2-49, this synthesis features a phosphine-catalyzed [3 + 2]cycloaddition reaction?Curtius rearrangement reaction ? Intramolecular Aldol condensation reaction and oxidative rearrangement reaction of tertiary allylic alcohol by PCC, meanwhile lays a solid foundation for the total synthesis of Daphlongamine E.
Keywords/Search Tags:Daphlongamine E, alkaloids, [3+2] cycloaddition reaction, Aldol condensation reaction, Curtius rearrangement reaction, Oxidative rearrangement reaction
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