Transcript Structural analysis

Structural analysis
H
H
H
C
H3C
CH3
H3C
CH3
H
H3C
H3C
H3C
CH3
CH3
CH3
CH3
H3C
CH3
H3C
CH3
CH3
H3C
H3C
“Molecular Dog” by Robert Chambers
H
H
N
Zoloft
Cl
Cl
H
N
H
Amphetamine - obesity treatment
O
N
Diethylpropion - obesity treatment
OH
H
Dronabinol
H
O
O
O
CH3
H
N
Ritalin
O
HO
OH
NH2
HO
Levodopa
O
O
O
NH
O
O
OH
O
OH
HO
O
Taxol
From the bark of the Pacific
yew tree (kills the tree to
harvest enough); or a closely
related compound from the
needles of the European yew
tree (doesn’t kill the tree).
O O
O
O
C&E News July 7, 2008 Volume 86, Number 27 p. 88 : an example from an
illustration for a book review in the New York Times. What do you think of this
as a chemical structure???
(What do you surmise the book was about?)
When seas become deadly…
O
HO
C
H3C
H
O
O
H
H
H
CH3
CH3
H3C
H
O
O
H
H
CH3
H
O
H
O
O
H
O
O
H
O
H
O
O
H
H
H
Brevetoxin B
H
CH3
CH3
How many carbons in a row can you count in this molecule?____
H2C
H2C
CH3
O
CH3
HO
CH3
H3C
O
O
O
O
O
O
CH3
CH3
N
OH
O
HO
O
H3C
CH3
Tacrolimus - immunosuppressant
for organ transplantation
H3C
CH3
CH3
CH3
OH
Vitamin A (trans-retinol)
CH3
The following slides are examples to
consider how molecules get converted
from one to another.
Example 1:
cis/trans
isomerization
OH
Example 2:
OH
OH
HO
OH
OH
HO
Vescalene
O
O
O
HO
OH
O
O
O
O
O
O
O
OH
HO
OH
HO
OH
Castalagin
O
O
O
OH
OH
O
OH
O
O
OH
HO
OH
HO
OH
HO
OH
HO
OH
OH
Starting point: Molecule from oak-barrel-aged wine
Target molecule:
Potential potent
topoisomerase II inhibitor
OH
HO
OH
OH
OH
OH
HO
OH
O
HO
O
O
O
O
O
Acid hydrolysis
OH
Castalagin
O
OH
OH
O
O
of two esters
O
O
O
O
O
OH
HO
O
O
OH
OH
HO
HO
OH
HO
OH
OH
HO
OH
HO
OH
OH
OH
1st intermediate
OH
OH
OH
OH
OH
O
O
O
OH
O
OH
Epimerization
O
O
O
O
at a chiral center
OH
HO
O
O
OH
O
O
OH
HO
OH
HO
OH
HO
OH
OH
OH
HO
OH
HO
OH
OH
1st
intermediate
2nd intermediate
(Change of stereochemistry = epimerization)
OH
OH
OH
OH
OH
O
O
O
O
OH
Elimination
O
O
OH
HO
O
O
O
O
(Dehydration)
OH
O
O
OH
HO
OH
HO
OH
HO
OH
OH
OH
2nd intermediate
HO
OH
HO
OH
OH
Vescalene
Example 3:
Prostratin (a molecule with potential to pull HIV out of hiding so it can
be eliminated) can be synthesized from phorbol in several steps.
What steps would be necessary to change the molecule phorbol into
the molecule prostratin?
Phorbol: available from feedstock in quantity
Prostratin: found in a Samoan rainforest tree; not available from that
source in sustainable quantity