Structural analysis
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Structural analysis. “Molecular Dog” by Robert Chambers. 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).

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Structural analysis

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Structural analysis

Structural analysis


Structural analysis

“Molecular Dog” by Robert Chambers


Structural analysis

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).


Structural analysis

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?)


Structural analysis

When seas become deadly…

How many carbons in a row can you count in this molecule?____


Structural analysis

The following slides are examples to consider how molecules get converted from one to another.


Structural analysis

Example 1: cis/trans isomerization


Structural analysis

Example 2:

Target molecule:

Potential potent topoisomerase II inhibitor

Starting point: Molecule from oak-barrel-aged wine


Structural analysis

1st intermediate


Structural analysis

1st intermediate

2nd intermediate

(Change of stereochemistry = epimerization)


Structural analysis

2nd intermediate

Vescalene


Structural analysis

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


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