Group Meeting Problems
February 28, 2007
1. Show the mechanism for the following transformation.
1. PhNMe2, heat
2. O3
O
O
3. H3PO4
O
O
O
O
2. Barriault and Deon recently reported the following transformation in conjunction with their
synthesis of arteanniun M (Org. Lett. 2001, 3, 1925-1927). Provide a mechanism for the
illustrated thermal rearrangement(s) of A to B. Where the stereochemical issues are at stake,
provide clear three-dimensional drawings to support your answer.
H
Me
Me
N
H
N
Single product
diasteromer
Toluene, 120oC
OR
OH
OH
OR
3. Fill in the boxes with the appropriate structures to obtain an acetyl cholinesterase inhibitor, a
promising pro-drug to treat Alzheimer Disease.
O
O
OH
+ H
+ H2N NH2
Base
O
POCl3
DMF
+
reflux
C24H29N5
AChE inhibitor to treat AD
Br
LiAlH4
H
N
+
+
N
H
NC
Cl