Wednesday, January 1, 2014

Obligatory Favorite Papers Post

It seems like everyone out there is making Top 10 lists of some sort. We like to be nontraditional here, so a few of us have put together some of our favorite papers with absolutely no reason, rhyme, or order. And we even waited until the actual end of 2013. We present some of our favorite total syntheses, and some of our favorite methods, in no particular order.

Enantioselective Synthesis of Pactamycin, a Complex Antitumor Antibiotic - Jeff Johnson's 15-step synthesis of a nightmarish looking cyclopentane features an enantioselective Mannich reaction and a nifty diasteroselective reduction.

Total Synthesis of (-)-Nakadomerin A - A 10-step synthesis of an awesome molecule from Dave Evans. That's all that needs to be said.

Total Synthesis of 6-Deoxyerythronolide B via C–C Bond-Forming Transfoer Hydrogenation - A 14-step synthesis of a famous target using Ir and Ru catalysis developed by Michael Krische. While I struggle with "1500 mol%", the chemistry is great.

Nine-Step Enantioselective Total Synthesis of (-)-Vincorine - Legend has it that Dave MacMillan eats strychnine, and that is the source of all of his power. I made that up, but this 9-step synthesis might make you believe it.

Catalytic Activation of Carbohydrates as Formaldehyde Equivalents for Stetter Reaction with Enones - The Stetter reaction is pretty much as old as dirt, but getting formaldehyde to cooperate has been a problem. Yongghui Chi came up with a cool solution and used carbohydrates as surrogates to accomplish the same sort of transformation.

Enantio– and Diastereodivergent Dual Catalysis: Allylation of Branched Aldehydes - Racemic starting materials plus chiral non-racemic catalysts equals all of the stereoisomers. Carreira keeps dropping these knowledge bombs on the chemistry world, and I hope he doesn't stop any time soon.

A Catalytic Enantioselective Tandem Allylation Strategy for Rapid Terpene Construction: Application to the Synthesis of Pumilaside Aglycon - Enantioselective diboration of dienes followed by addition of a dicarbonyl compound leads to not one, but two allylation reactions. Morken then applies this nifty method to the synthesis of a small terpene.

Catalytic Synthesis of n-Alkyl Arenes Through Alkyl Group Cross-Metathesis - A tandem dehydrogenation/metathesis/hydrogenation sequence is used to couple ethylbenzene to various alkanes. Schrock and company have also found catalysts that are stable to the high temperatures and long reaction times, paving the way for rendering alkyl metathesis as useful as olefin metathesis.

There you go. Some of our favorite papers. Now everyone have a happy new year, and do good science in 2014!

1. Credit to Google for the image.

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