Sengupta, Sandip Bae, Munhyung Oh, Dong-Chan Dash, Uttam Kim, Hak Joong Song, Woon Young Shin, Injae Sim, Taebo 2024-01-20T00:01:24Z 2024-01-20T00:01:24Z 2022-01-10 2017-12 0022-3263 https://pubs.kist.re.kr/handle/201004/121960 Total synthesis of the proposed structure of baulamycin A was performed. The spectral properties of the synthetic compound differ from those reported for the natural product. On the basis of comprehensive NMR. study; we proposed two other possible structures for natural baulamycin A. Total syntheses of these two substances were performed, which enabled assignment of the correct structure of. baulamycin A. Key features of the convergent and fully stereocontrolled route include Evans Aldol and Brown allylation reactions to construct the left fragment, a prolinol amide-derived alkylation/desymmetrization to install the methyl-substituted centers in the right fragment, and finally, a Carreira alkynylation to join both fragments. In addition, we have determined the inhibitory activities of novel baulamycin A derivatives against the enzyme SbnE. This SAR study provides useful insight into the design of novel SbnE inhibitors that overcome the drug resistance of pathogens, which cause life-threatening infections. English American Chemical Society Structural Revision of Baulamycin A and Structure-Activity Relationships of Baulamycin A Derivatives Article 10.1021/acs.joc.7b01719 1 Journal of Organic Chemistry, v.82, no.24, pp.12947 - 12966 Journal of Organic Chemistry 82 24 12947 12966 N scie scopus 000418392600001 2-s2.0-85038435875 Chemistry, Organic Chemistry Article ENANTIOSELECTIVE TOTAL-SYNTHESIS PATHOGEN STAPHYLOCOCCUS-AUREUS ANTI-ALDOL REACTIONS BACILLUS-ANTHRACIS STEREOSELECTIVE-SYNTHESIS SIDEROPHORE BIOSYNTHESIS PETROBACTIN BIOSYNTHESIS ABSOLUTE-CONFIGURATIONS ASYMMETRIC-SYNTHESIS CITRATE SYNTHASE Baulamycin Structural Revision Total Synthesis