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ChemInform Abstract: Total Synthesis of Vancomycin Aglycon. Part 3. Final Stages.

✍ Scribed by K. C. NICOLAOU; M. TAKAYANAGI; N. F. JAIN; S. NATARAJAN; A. E. KOUMBIS; T. BANDO; J. M. RAMANJULU

Publisher
John Wiley and Sons
Year
2010
Weight
27 KB
Volume
30
Category
Article
ISSN
0931-7597

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✦ Synopsis

Total Synthesis of Vancomycin Aglycon. Part 3. Final Stages.

-The conversion of the skeletal framework (preceding paper) to the vancomycin aglycon is started by the substitution of the triazene moiety with a hydroxyl group. The triazene moiety is successfully reduced to an amino group by Raney nickel that also causes a partial debenzylation. The desired phenol is prepared via its boronate by further elaboration of the amino group. After protection of the phenolic hydroxyl group the oxidation of the homobenzylic alcohol to a carboxyl group is achieved with Dess-Martin reagent. Finally, all protecting groups are removed by treatment with AlBr 3 and EtSH furnishing the target aglycon. -(NICOLAOU, K.

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