Vancomycin is an important antibiotic. It is isolated from the bacterium Streptomyces orientalis and functions by inhibiting bacterial mucopeptide synthesis. It is a last line of defense against the resistant Staph organisms that are now common in hospitals. OH HO, OH H. NHME NH H NH HO,C- “NH2 Vancomycin aglycon ОН НО In 1999, Professor Dale Boger (The Scripps Research Institute) reported a synthesis of vancomycin aglycon (aglycon = lacking a sugar) involving the following steps, among others. Compound (I) was prepared from simple starting materials by a series of steps involving forming amide bonds. Suggest reasonable precursors and show how the bonds could be formed (the actual reagents used have not been introduced, but they work in a similar way to those you know). NO, OMe F HO, TBDMSO D P = Protecting Group %3D MeOOC NHP Br OMe Compound (I) was then converted into (II).
Vancomycin is an important antibiotic. It is isolated from the bacterium Streptomyces orientalis and functions by inhibiting bacterial mucopeptide synthesis. It is a last line of defense against the resistant Staph organisms that are now common in hospitals. OH HO, OH H. NHME NH H NH HO,C- “NH2 Vancomycin aglycon ОН НО In 1999, Professor Dale Boger (The Scripps Research Institute) reported a synthesis of vancomycin aglycon (aglycon = lacking a sugar) involving the following steps, among others. Compound (I) was prepared from simple starting materials by a series of steps involving forming amide bonds. Suggest reasonable precursors and show how the bonds could be formed (the actual reagents used have not been introduced, but they work in a similar way to those you know). NO, OMe F HO, TBDMSO D P = Protecting Group %3D MeOOC NHP Br OMe Compound (I) was then converted into (II).
Chapter24: Amines And Heterocycles
Section24.SE: Something Extra
Problem 38MP
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Transcribed Image Text:Vancomycin is an important antibiotic. It is isolated from the bacterium Streptomyces
orientalis and functions by inhibiting bacterial mucopeptide synthesis. It is a last line of
defense against the resistant Staph organisms that are now common in hospitals.
OH
HO,
OH
H.
NHME
NH
H
NH
HO,C-
“NH2
Vancomycin aglycon
ОН
НО
In 1999, Professor Dale Boger (The Scripps Research Institute) reported a synthesis of
vancomycin aglycon (aglycon = lacking a sugar) involving the following steps, among
others. Compound (I) was prepared from simple starting materials by a series of steps
involving forming amide bonds.
Transcribed Image Text:Suggest reasonable precursors and show how the bonds could be formed (the
actual reagents used have not been introduced, but they work in a similar way to
those you know).
NO,
OMe
F
HO,
TBDMSO
D
P = Protecting
Group
%3D
MeOOC
NHP
Br
OMe
Compound (I) was then converted into (II).
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