Jared Shaw (aka shawshankrxn.bsky.social)
@shawshankrxn
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pretty much done with the dumpsterfire formerly known as twitter! 😎 *keeping this handle in the event that Darth Elon sells, retires or dies*
Davis, CA
Joined August 2015
Been a while since I posted anything, but I have an incredible PhD student who is graduating shortly and looking for opportunities in industry...email me for details if you have an opening!
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The annual Shaw/@AnnalieseFranz group BBQ and homecoming is this Saturday! I've tried to send to all former group members, but don't have emails for everyone...happy to send evite if you dm me and it's in the usual spot if you want to just stop by!
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Are you an alum of the @UCDChem graduate program? If yes, please check out this wonderful resource put together by Dr. Sundeep Dugar!
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Hey #chemtwitter...anyone ever find a good vendor for enantiomerically pure naringenin? Some places sell stuff listed as single enantiomer, but the stuff in the bottle is actually racemic! 😱
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seems like scifinder has spoken...occurrence in journals: carbocycle: 12,086 carbacycle: 26 carbocyclic: 7,595 carbacyclic: 55
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@awhspeed We'll try deuterating first and if that works well, we'll try a series of electrophiles!
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@mx_million @CRP_Laboratory We've chatted...I don't think he's doing a lot of e-chem at the moment, but another twitter user has offered to run some reactions so we'll see if e-chem prevails!
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@ACS_DivBioChem Yes! I'm definitely willing to send SM and prod to others who dabble! a friend at a company with a huge collection of oxidation enzymes ran a plate of obvious choices and got NR, so it would have to be someone with an enzyme with a good chance of working for this substrate!
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@Dny_Q I would be *very* interested in this! That said, I have a colleague at a company with a large oxidation enzyme collection and they sent through our substrate with one plate and got no reaction, but I will definitely DM you!
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@anniegorden weird...one other person mentioned not being able to DM but then later they did...would love to get an email on this: @jtshaw@ucdavis.edu?
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@CJohnsonChemist never tried, but the 3° CH might be a problem. I reached out to her directly and never heard back.
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@Varajay407 I think so...I have a giant sheet of these things and we either get competing 3° oxidation or a quinone-methide intermediate formed so that a carbonyl replaces the para methoxy group.
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@MatthewHorwitz1 This is a good idea, but this thing in on a knife's edge for fully aromatizing to the naphthalene, even though it's a little strained...we can actually isolate quinone methide products that form from the intermediate you have drawn!
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@awhspeed Interesting...we have not, but we have found that many benzylic single oxidations lead to unstable products with the doubly activated top substrate, so it would be a question of what electrophile to send in 🤔
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