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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111Diastereoselective and Enantioselective Syntheses
OMe
OMe
NH
2
Me
OMe
OMe
NHBoc
Me
MeO
2
C
CO
2
Me
NHBoc
Me
HO
2
C
NHBoc
Me
1. Boc
2
O, NaOH
dioxane, 3 h
0°C
2. Na/NH
3
/ether
EtOH, –78°C, 2 h
1. O
3
, EtOH, –78°C
2. H
2
, Pd/C, –78°C RT
RT
1. DMSO, H
2
O/NaCl
reux, 2 h
2. aq. KOH, RT, 1 h
3. 2N HCl
142 143
144 145
84%
98%
92%
67%
An interesting transformation used citronellic acid (146, derived from pulegone)
90
as a template. The acid moiety was converted to an amine and the alkene moiety was
converted to a nitrile and thereby to an acid.
91
This transformation was accomplished
by reaction of 146 with urea to give 147, and reduction followed by acylation and
ozonolysis (with a reductiv ...
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