October 2013
Intermediate to advanced
242 pages
9h 22m
English
Content preview from Methods of Non-a-Amino Acid Synthesis, 2nd Edition
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159Biologically Important Amino Acids
CHO
H
2
N
H
2
N
O
O
H
2
N
O
O
H
2
N
O
HO
Me
N
O
Boc
O
H
CHO
Me
OH
OH
SiMe
3
+
173
p-TsOH, reux
TiCl
4
, CH
2
Cl
2
–78°C
1. O
3
; Me
2
S
2. PCC
1. Bn
2
NH•TFA
2. PrNH
2
, HCN
3. NaCN, )))))))
4. aq. NaOH
5. aq. HCl
187 188
189 190
84%
(71%)
186
Other amino acid precursors have been used for synthesis. The α-amino acid
valine was converted to statine via initial condensation of the ethyl ester of valine
with 191 to give 192.
211
Heating this adduct in methanol led to lactam 193, which was
reduced to 194. Hydrolysis gave statine, in 63% overall yield from valine.
H
2
N
CO
2
Et
O
O
O
O
HO
BocHN
O
O
O
O
N
N
CO
2
H
H
2
N
OH
Boc
OH
O
Boc
O
OH
+
191 19
21
93
194 173
1. DMAP
2. IPCF
reux
NaBH
4
AcOH
1. NaOMe
2. TFA ...
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