Jasmone 1 - ChemistforChrist

Synthesis of JASMONE
Chiral Hydrazones: Enders
N N
OMe
Is made out of proline
by reduction and protection
with MeI
1
2
3
O
1
2
O
O
3
N OMe
Me
Weinreb-Amid
1.) n-BuLi
2.) E
3.) H 3O , CuSO 4
+ X
Wittig-Reaction
O
O
X
O
+
+
O
XMg
+
O
H 2 , Lindlar-Pd
PPh 3
Aledehyde reacts faster than the ketone!
O
Commercially available
E
*
SAMP RAMP
N
H
O Mg
N O
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R
Problem:
E/Z Isomers
S or R
OMe Amino
Methoxy
Pyrolidine