Chemistry Reference
In-Depth Information
5.48
Muscarine is chiral. The compound has three different stereogenic centers, indicated
in the formula below. There are therefore 2
3
or 8 possible stereoisomers.
H
HO
R
+
H
C
S
C
2
NC
(
3
)
3
3
S
-
O
H
H
H
The configurational designation (
R
or
S
) at each stereogenic center in the naturally
occurring poison is shown.
5.49
NO
2
R
HO
H
R
H
NHCOCH Cl
2
CH
2
OH
5.50
The one stereogenic center in methoprene has
S
configuration:
C
H
3
O
C
H
3
H
3
C
H
3
C
C
H
3
H
H
3
C
S
O
O
C
H
3
5.51
a.
The stereogenic center is marked with an asterisk and the priorities of the
4 groups are:
3
CH
3
4
H
*
1
O
CO
2
H
2
O
H C
3
HO
OH
So, the absolute configuration is
S
.
b.
The additional stereogenic carbons, and their configuration, in daumone are:
CH
3
H
O
CO
2
H
S
R
*
*
O
H C
3
HO
*
R
R*
OH
