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Chemistry Forums for Students => Organic Chemistry Forum => Topic started by: Altered State on January 13, 2015, 11:02:05 AM

Title: POTW 12-01-2015
Post by: Altered State on January 13, 2015, 11:02:05 AM

Here is this week's target, rules can be found here. http://www.chemicalforums.com/index.php?topic=77867.msg284036#msg284036

Here is this week problem:

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2F77MmZbX.jpg&hash=4a71ec7071d515960e91f4b8b40a8d1229cd4702)



Maybe too many stereocenters?
Well, I propose something like this because I want to improve my knowledge about stereochemistry control, an seeing examples is one of the best ways to do so, but feel free to propose non-stereoselective approaches too, I'll probably do one myself.

Title: Re: POTW 12-01-2015
Post by: critzz on January 14, 2015, 06:52:06 PM

Wow, nice molecule, lots of functional groups (does it even exist? ^^).
I always like challenges, so here is my asymmetric synthesis proposal:

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi59.tinypic.com%2F2vv9k03.jpg&hash=e7962b36e3c1f9d24409b486e9b49fc3be12fa64)

Title: Re: POTW 12-01-2015
Post by: kriggy on January 15, 2015, 12:35:12 AM

We have almost exactly the same path to make the heterocyclic part. I´ll post my way later today (It lacks some stereochemistry control :/ )

Title: Re: POTW 12-01-2015
Post by: kriggy on February 04, 2015, 09:41:14 AM

It looks like its dying a bit.. :(
Sorry, it took me bit longer than I expected.. Not much stereochemistry control on my part, im seriously lacking in the area.

(https://www.chemicalforums.com/proxy.php?request=http%3A%2F%2Fi.imgur.com%2FJ8rfLuX.png&hash=73b115d8ee17b6b734a67601671e93924c07b71e)]

The 1st equivalent of grignard is to neutralize the COOH group. Im thinking that some stereochem control could be implemented but yea.. not today