Methods of Non-a-Amino Acid Synthesis, 2nd Edition

26

Methods of Non-α-Amino Acid Synthesis, Second Edition

moiety. The nal product was 2-hydroxy-4-aminobutanoic acid (145).

132

It is noted that

the aminoglycoside antibiotic pyrankacin contains the 4-amino-2-hydroxybutanoic

acid unit (145).

133

H

2

N NH

2

HO NH

2

CO

2

H CO

2

H

144

145

NaNO

2

H+

3-Amino-4-oxoamino acids have been prepared by refunctionalization of

L-homoserine. Conversion of homoserine to the N-benzenesulfonamide allowed a

nickel-catalyzed reaction with various alkyl Grignard reagents to give the amido-

ketone.

134

Jones oxidation

135

of the primary alcohol moiety was followed by deprot-

ection to give the targeted 146. This amino acid was used to ...