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


“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).


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…

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


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


Example 1: cis/trans isomerization


Example 2:

Target molecule:

Potential potent topoisomerase II inhibitor

Starting point: Molecule from oak-barrel-aged wine


1st intermediate


1st intermediate

2nd intermediate

(Change of stereochemistry = epimerization)


2nd intermediate

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


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