Abstract
A stereoselective approach to the core structure of polyoxin and nikkomycin antibiotics has been developed. The key steps of this approach include diastereoselective nucleophilic addition of 2-lithiofuran to tert-butanesulfinyl imine derived from (S)-tert-butanesulfinamide and ribosyl aldehyde for the generation of C-5 stereocenter, and the use of triflic acid to remove tert-butylsulfonyl group. Significantly, the synthesis provides a method for large-scale preparation of polyoxin and nikkomycin analogues because of simple operation, excellent yield and high stereoselectivity.
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