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...
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.
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.
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
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