OH OH HO NHMe NH NH HOC vancomycin aglycon OH OH In 1999, Professor Dale Boger (

Question

OH OH HO NHMe NH NH HOC vancomycin aglycon OH OH In 1999, Professor Dale Boger (he Scripps Research Institute) reported a synthesis of vancomycin aglycon aglycon lacking a sugar) involving the following steps, among others. Compound (D was prepared from simple starting materials by a series of steps involving forming amide bonds. formed (the (a suggest reasonable precursors and show how the bonds could be similar way actual reagents used have not been introduced, but they work in a to those you know). OMe OH HO. TBDMSO P m Protecting Group NHP OMe Compound (D was then converted into a (b) Give reagents for this reaction and suggest the mechanism. OMe OH TBDMSO P Protecting Group NHP OMe

Explanation / Answer

1/ Compound 1 to Compound 2 ---> Nitratinf mixture (conc HNO3 and conc H2SO4)

2. Compound 2to Compound 3----> heat -condensation and elimination of HF in the presence of a base

3. Compound 3---> compound 4---->a Grignardreagent of ring Fragment A in dry ether followed by acid hydrolysis.

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