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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134
Methods of Non-α-Amino Acid Synthesis, Second Edition
Emmons reaction
85
with paraformaldehyde led to formation of the alkene moiety in
59. Deprotection gave 60, which was utilized in the preparation of 61.
SO
2
Ph
NHBoc
N
P
O
OMe
OMe
O
N
P
O
OMe
OMe
O
BocHN
+
CO
2
Me
NHBoc
CO
2
H
NH
2
56
57
58
59 60
thiourea
catalyst
K
2
CO
3
1. 2.2 NaOMe, THF, –15°C
2. 5 (HCHO)
n
, –15°C
1. 1.5 LiOH, THF
2. HCl, EtOAc
O
O
O
O
H
N
O
O
OH
O
N
H
NH
O
N
O
HO
H
2
N
61
Several ω-N-quinone amino acids have been prepared from β-alanine, 4-aminobu-
tanoic acid, 5-aminopentanoic, and 6-aminohexanoic acid.
86
These amino acids were
used for post-chain assembly modications of bioactive peptides known to target can-
cer-damaged area ...
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