Organic Synthesis

1
Organic Synthesis
chemists
?
Molecular things you want
2
Molecular things you want
Molecular things you have
3
Synthesis Requires Two Things
1. a library of reactions
2. a strategy or plan for combining known
reactions to reach the desired target
molecule
3. and a little luck always helps
4
goal
(a desired molecular structure)
5
Work the problem from the final goal toward the
reactants.
Have a library of reactions that connect a goal
to a subgoal.
goal
6
Work the problem from the final goal toward the
reactants.
Have a library of reactions that connect a goal
to a subgoal.
Using your knowledge of each reaction select the
best pathway as your solution to the synthetic
problem.
7
Work the problem from the final goal toward the
reactants.
Have a library of reactions that connect a goal
to a subgoal.
Using your knowledge of each reaction select the
best pathway as your solution to the synthetic
problem.
8
Discodermolide
The result of biological studies stimulated
considerable interest in discodermolide as a
possible immunosuppressant.
Subsequently studies demonstrated discodermolide
is a potent cell growth inhibitory agent, which
arrests cell development at the M phase by
binding and stabilizing mitotic spindle
microtubules. Thus, the ability of ()-1 to
inhibit cell growth was suggested to resemble the
clinically proven anticancer agent Taxol.
9
Discodermolide
10
Discodermolide
Some problems with pharmaceuticals from natural
sources
Quantities can be very limited.
The isolation process can be very expensive.
Industrial production can destroy valuable
ecosystems.
More active structural variants are not available
from nature.
11
Discodermolide
Some problems with pharmaceuticals from natural
sources
Quantities can be very limited.
The isolation process can be very expensive.
Industrial production can destroy valuable
ecosystems.
More active structural variants are not available
from nature.
12
Discodermolide
13
Discodermolide
chemical synthesis
available chemicals
14
Discodermolide
chemical synthesis
15
commercially available
16
A Library of Reactions
17
General Scheme of a new reaction
18
Example.
muscalure, the sex attractant of the common
housefly
19
A Library of Reactions
20
General Reaction Scheme of a new reaction
21
Problems in synthetic chemistry
Work the problem from the final goal toward the
reactants.
Have a library of reactions that connect a goal
to a subgoal.
Using your knowledge of each reaction select the
best pathway as your solution to the synthetic
problem.
22
?
23
(No Transcript)
24
(No Transcript)
25
(No Transcript)
26
(No Transcript)
27
(No Transcript)
28
(No Transcript)
29
(No Transcript)
30
(No Transcript)
31
(No Transcript)