Wednesday, April 23, 2014

Chlorination War Club

Ever wonder what kind of name is palau’amine?
Well yes… this alkaloid was isolated from a sea sponge native to the island nation of Palau.

Tuesday, April 8, 2014

Electrochemical Synthesis of Dixiamycins

Phil Baran upon learning about electrochemistry

UPDATE: Our paper was highlighted on Deadspin!
UPDATE 2: Support from the San Diego Chargers!

Our paper on the total synthesis of dixiamycin B is now live in the JACS ASAP section, which means it's my turn to write a blog post. When we initiated this project, we had no idea we'd turn to electrochemistry; we just thought making the N–N bond would be interesting. In fact, I remember it like it was yesterday...

[Professor enters from stage left]
Professor: How would you make this?!
Student: Probably from hydrazine.
Professor: That's not interesting!
[Professor exits stage left]

Monday, March 31, 2014

Playing with radicals

Aromatic C–H amination has received a lot of attention over the last few years, and our efforts began late 2012. The goal was simple: create a nitrogen-centered radical and trap it with a heterocycle.

Wednesday, March 19, 2014

Oxidative Explorations of Taxanes

Our paper is now out. This ongoing project, although some might label as simple, requires many different types of oxidations, and all of which require many experiments to discover. You can read the paper and ask me questions or send me comments to your heart’s content, but in this post I will talk about the discovery process and tell some of the stories.

Tuesday, March 18, 2014

Open Flask Blog Turns 1

On a fateful day last February, Y. Brando, Dane, Will, and Hans were busy sitting around rumor-mongering upon the latest internet gossip (likely started by Hans in the first place). Dane was dwelling over his lack of Reddit karma when they were all interrupted by Mr. Phil Barden. Surprising all parties involved, as usual, P.S.B. suggested "if you can't beat them, join them." And thus, we invented Openflask. Our first post was on 2/26/2013. And in true fashion of a graduate student, we forgot its birthday.

Wednesday, March 12, 2014

Magic Methyl Effect

Character picture taken from “Wreck It Ralph”
      This week, the newest paper in our sulfinate chemistry series was published online, featuring a radical-based C–H methylation of heterocycles. Indeed, as we embarked on “mission methylation,” we were mesmerized by the “magic methyl effect” where appending a single methyl group in the appropriate place could improve the biological activities of pharmaceuticals as much as 100-fold. (See the elegant review by Tim Cernak: Angew.Chem. Int. Ed. 2013, 52, 12256; there are also two interesting blog entries “In the Pipeline” about the Magic Methyl Group in 2011 and 2013.

Tuesday, March 11, 2014

Lady Luck Deserves Her Citations Too

There's no luck in science.1 Rather than say we scientists are lucky or fortunate to find some interesting reactivity (to look specifically at the chemistry sides of science), we have to say we designed it, or at least designed the screening process by which we found it. Rather than “discover” things, we “engineer” or develop” them. We “invent” rather than “stumble upon” reactions, if we are to believe our own writing. Heck, we even have to claim we're accelerating serendipity,2 as if the notion of manipulating serendipity didn't change its meaning altogether (the opposing meanings does make it a catchy title though). An ironic aspect of this phenomenon, especially in the field of organic synthesis, is that removing words like “discover” from our manuscripts makes us sound even more like engineers rather than practitioners of basic science.