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Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment

Total synthesis of everninomicin 13,384-1--Part 2: synthesis of the FGHA2 fragment

Chemistry 6(17): 3116-3148

The stereoselective synthesis of everninomicin's 13,384-1 (1) FGHA2 fragment (2) in a suitable form for incorporation into the final target (1) is described. The construction of the FG 1,1'-disaccharide linkage relied on a new method based on tin-acetal chemistry, while for the GH orthoester bridge, a number of approaches were explored. Final success for the latter construction came when a novel 1,2-phenylseleno migration reaction was applied to couple rings G and H, followed by ketene acetal and orthoester formation.

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Accession: 047802736

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PMID: 11002993

DOI: 10.1002/1521-3765(20000901)6:17<3116::aid-chem3116>3.0.co;2-8

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