Enantioselective Total Synthesis Of Ileabethoxazole

With the widespread use of drugs,the emergence of multidrug-resistant tuberculosis and XDR-TB has made tuberculosis a global health problem that threatens human health.Therefore,it is particularly important to develop a new type of anti-tuberculosis drug with strong drug efficacy,small side effects and short cycle.ileabethoxazole is a marine benzoxazole alkaloids isolated from the Caribbean Sea whip by Rodriguez and co-workers.Notably,1 shows significant antimicrobial activity against M.tuberculosis.Its valuable potentials to development of anti-TB drugs stimulated broad attentions from synthetic organic community.In this thesis,we introduced the isolation,activity,tructural characteristics of Ileabethoxazole and the asymmetric allylation reaction.In addition,we summarized previous synthetic synthesis strategy of Ileabethoxazole.Finally,asymmetric total synthesis of the natural product Ileabethoxazole was achieved in 16 steps starting from compound 7.The main method is the Ir/chiral amine double-catalyzed asymmetric allylation reaction developed by the Carreira group,the positive ion cyclization reaction and the Friedel acylation reaction,etc.and also a new version of cationic cyclization,which could be stereocontrolled through?-?interactions.Addition,our prochedure for the introduction of methyl at C₄ affoded feasible pathway to structural modifications at C₄ for 1...