3 years ago

Amipurimycin, total synthesis of the proposed structures and diastereoisomers

Shengyang Wang, Xin Cao, Biao Yu, Qingju Zhang, Jiansong Sun, Yachen Zhao, Gongli Tang
The proposed diastereoisomers (1a-1d) together with their C8'-epimers (1e-1h) of amipurimycin, a unique antifungal peptidyl nucleoside antibiotic, have been synthesized for the first time. The synthetic approach is efficient and stereo-divergent, featuring a stereoselective aldol condensation to build the branched C9 sugar amino acid skeleton and a regio- and stereo-controlled gold(I)-catalyzed N-glycosylation to furnish the purine nucleoside. Analysis of the NMR data suggests that the previously assigned configuration of the tertiary C-3' in amipurimycin should be inverted.

Publisher URL: http://onlinelibrary.wiley.com/resolve/doi

DOI: 10.1002/anie.201800169

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