Jasmone 1 - ChemistforChrist

Synthesis of JASMONE
Synthesis:
EtO
O
O
O
O
O
1
2
H 2N NMe 2
O
100%
90%
+
N NMe 2
O
10%
Enolate formed at Position: 2 1
electron poor due
to conjugation
R
R
O O
E 2
O
E 1
:
1. O 3
2. Me 2S
O
O
Ph 3P
Sterically hindered Base
(Kinetically controlled deprotonation)
NaOH
to create the
Ylide
: Thermodynamically controlled deprotonation
R
R
For E 1 = Br
For E 2 =
Br
BH 4
H 3O
- CO 2
O
EtO
EtO
O O
O O
E 2
R
E 1
R
n-Bu Li
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Li
E 2
1. n-BuLi
2.
O
3. H2O + Cu(OAc) 2
O
75%
SiMe3 N
SiMe3 EtO
EtO
E 1
O O
O O
NaOH
70%
44% yield
LMDS
R
O
OH
O
O
What was deprotonated
last will react first!
E 1
R
Oxidation
with PCC