Total Synthesis of UCS1025A via Tandem Carbonylative Stille Cross Coupling and Diels-Alder Reactiont  

作　　者：Chengsen Cui Mingi Dai 

机构地区：[1]Deparment of Chemistry and Center for Cancer Research Purdue University West Lfaytte,IN 47907,United States [2]Department of Chemistry,Emory University,Atlanta,GA 30322,United States

出　　处：《Chinese Journal of Chemistry》2023年第22期3019-3024,共6页中国化学（英文版）

基　　金：supported by NSF 2102022.

摘　　要：We report an efficient and convergent strategy for the total synthesis of UCS1025A and its diastereomer tetra-epi-UCS1025A.Ucs1025A is a representative member of the naturally occurring pyrrolizidinone polyketides,from which members with potent antibacterial,antifungal,and anticancer activities have been identified.Our approach features a tandem carbonylative Stille cross coupling and Diels-Alder reaction to forge a key C-C bond and build the trans-decalin system.This tandem process utilizes carbon monoxide as a one-carbon linchpin to stitch a vinyl triflate and a vinylstannane together and form the desired enone moiety for the subsequent intramolecular Diels-Alder cyclization.Our synthesis also provides a versatile approach for the synthesis of other related pyrrolizidinone-containing polyketides.

关 键 词：Natural products Total synthesis UCS1025A CARBONYLATION Diels-Alder reaction Tandem reaction 

分 类 号：O62[理学—有机化学]