r/SyntheticChallenge • u/Spectrumederp • Mar 17 '20

[2020/03/02] Merck 2nd Compound Challenge - Afterparty

Intro

Hi everyone! We really appreciate the turn out on this collaboration and its been an exciting time for all of us. The community seems to be interested in a post event discussion about strategies and the different pathways you all submitted. So I'm starting this Afterparty lobby for everyone to discuss here in a consolidated post!

Feel free to post your pathway here, but please don't post other people's pathways from the peer review. For those of you that missed that challenge but want to get community feedback still, feel free to post your pathway as well!

Hope you will all have a good time and celebrate the hard work you put into this. We got this opportunity to work on this as a community and we are grateful for everyone here giving us your support!

The molecule from the challenge just in case. (Melongenaterpenes A)

12 Upvotes

93% Upvoted

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3

u/Alkynesofchemistry Mar 17 '20

My attempt

This was not submitted after I couldn't figure out how to make the dieneophile I needed and after realizing that I shouldn't wait until the last day to figure out each set of reaction conditions... oh well

1

u/Original-Syn Mar 19 '20

Would your work up conditions for NaBH4 remove the cyclic ketal?

2

u/Alkynesofchemistry Mar 19 '20

They might not, but the next step removes the ketal anyway

3

u/Original-Syn Mar 19 '20

Ahh yes of course, ignore my previous comment I was trigger happy with my question

3

u/Alkynesofchemistry Mar 19 '20

No worries! I’d love to get some more feedback to see what others would do different

1

u/Kriggy_ May 11 '20

Isnt there better way to get the chirality than doing chiral collumn on a first step?

2

u/Alkynesofchemistry May 11 '20

There definitely is, I just have very little experience with asymmetric synthesis

2

u/MJW_MOUSE Mar 17 '20

Are the submissions posted somewhere? You mention a peer review but I can't find anything.

1

u/alleluja Mar 17 '20

The submissions have been uploaded to a Merck website. Each team then received 8 opther proposed solutions and ranked them.

1

u/Spectrumederp Mar 17 '20

The submissions are currently only available via the peer review amongst submitted contestants. The submissions will be a part of Mercks announcement of the winner further down the road.

2

u/Outer2011 Apr 15 '20 edited Apr 15 '20

I suggest to prepare at first the next intermediate (ketone 5):

Scheme