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Topic: (+)-camptothecin  (Read 6129 times)

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Offline MissPhosgene

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(+)-camptothecin
« on: April 23, 2010, 11:09:08 PM »
Hello. This is for whoever things trying to figure out synthetic routes on paper is super fun. 

The molecule is called (+)-camptothecin.

Please don't post a previously published synthesis. I can put up more complex structures if that is wanted. 
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

Offline tmartin

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Re: (+)-camptothecin
« Reply #1 on: April 24, 2010, 09:18:33 AM »
A molecule of the week instead of a problem of the week, I like it!  Interesting molecule (although it has too many nitrogens and not enough oxygens or stereocenters for my liking  :P), I don't think about this type of molecules very much though.

Looking at it at first I would think you'd want to find a quick convergent way, and cut the molecule in half somehow.  I was thinking perhaps a cross-coupling of some sort, and then just an addition to form the amide.  I think the stereocenter would be pretty tricky to install, ethyl vs methyl (although I think I've seen some recent organocatalytic reactions that can proceed with high ee's), but when I searched to find the basics about this molecule, it shows a hydroxyl.  Is the stereocenter supposed to be an ethyl back and a hydroxyl group up?

Offline MissPhosgene

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Re: (+)-camptothecin
« Reply #2 on: April 24, 2010, 11:26:36 AM »
Yes, you are right about the stereocenter. I forgot to put it in. Oh no.

Sorry, sorry, sorry. That is a really important one.

Here is the right one:


 
Stereograms of the 32 crystallographic point groups: little bike wheels of cold, hard, pure rationality.

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