The difluoroethylator?

Over the past few years our laboratory has become interested in the radical functionalization of heterocycles. This started with arylboronic acids as radical precursors but recently developed into alkylsulfinate chemistry. The latest addition to our list of commercialized reagents is sodium difluoroethanesulfinate (DFES-Na), a difluoroethylating agent.

According to Sigma-Aldrich, DFES-Na sold out of stock within 1 week of being listed, and due to the incredible demand, they are targeting multi-kilo quantities. Metric tons of DFES-Na will likely be needed in the next 10 years. This is, of course, exciting news for us but we would also like this blog post to be exciting for you as well. So, we have put up another video. This one is about Qianghui (first author of the paper describing DFES-Na) running a difluoroethylation reaction and hopefully after watching this video, you will be running your own difluoroethylation, too!

 

Mechanism Apr. 06, 2013

Onward for the answer!

The Portable Chemist's Consultant

This is my first ever blog entry, let alone the Baran lab blog but on all blogs web-wide. I thought this would be a suitable entry to celebrate this landmark of mine. I (Yoshi) came to the Baran Lab in 2007 and obtained my PhD last year but I'm staying here longer for a pet project of mine. And Ana's. And most importantly for those of you who visit this page for Baran lab news: Phil's vision. Case in point: we have been writing a book mostly on heterocyclic chemistry and today is our official launch date. The book is called "The Portable Chemist's Consultant." This is not a hardcover book but is only offered on the iBookstore; we also have a website dedicated to it.  While you can find the book itself and the sample book in the former, and cool graphics and a comments page in the latter, on this blog I decided to put up a quick video of myself talking through the features of this electronic book while holding up my iPad. 

   

Here is an impromptu video taken by Phil using his iPhone... he just stormed into my working area, brought me into his office and said "let's take a video of you talking about the interactive features of this book. Starting... now." 

Maybe one day I'll take a better version of this video that has my iPad on a more stable platform and without me stuttering, but for now this will do. I just wanted to showcase here that this is a highly interactive book with all sections hyperlinked to each other and all references hyperlinked to the original literature source on the internet. As well as a lot of Phil Baran videos for those of you who are not fortunate enough to be in San Diego to attend his heterocycles class (which started today, coincidentally... or not). Check it out!  --Yoshi

Baran Lab to move to Wyoming

In light of recent blog posts, we would like to formally announce that our lab is moving to an abandoned home depot somewhere in rural western Wyoming.

Young Brando is "excited to have two full hoods to himself," and Taycoh said, "with the new space and low overhead costs, we should be able to have a lab of two- to three-hundred students."

The ATF will be providing funding for new research on the novel chemoselective syntheses of ethan-1-ol and ethan-2-ol.

Phil's children's love of adorable farm animals may have influenced the move.

Stay tuned for more information!

A Taxol synthesis is simple

I got the results back from NSF fellowship application today. I didn't get the fellowship, but that doesn't matter. Something funny was that one of the reviewers said my “proposed project looked simple or at least written that way.”

I’m the chump working on the taxane project. The overall goal is in the figure below. You might have seen the Nature Chemistry paper where we described the construction of the taxane skeleton. My project involves multiple C-H oxidation transformations on this skeleton en route to Taxol. Simple, right?

I’m not here to toot my own horn or rally up a pity party, but I think every chemist familiar with synthetic organic chemistry will agree this endeavor is somewhere between crazy difficult and flat-out impossible. No one would claim it looks simple. Then why is this NSF reviewer judging my application if they don’t see the difficulty of this project?

To be clear, I wouldn't care if I scored “excellent” on everything and still didn't get the fellowship. There are many people deserving of this award, and who am I to say I deserve it more than anyone else? Also, there are plenty of reasons to not fund me or this project. My problem is that reviewers are unqualified to judge my “intellectual merit” if they don’t know the basic frontiers of my field. I guess the moral of the story is don’t assume people know why your science is hard. Be very explicit. This problem probably applies to some extent to other award applications and even applying for a job.

Column Chromatography....seems silly now.

Last month the team at Eisai responsible for the commercial scale synthesis of Halaven (easily the most complex drug molecule produced entirely by chemical synthesis) published a series of papers (theres three links there) detailing the development from the medchem route to process.  While these papers are a must read from the standpoint of using total synthesis to solve a supply need, this post is only peripherally related.

Early on in the synthesis of one of the pieces of the western half of the molecule the group does a chromatographic resolution of a racemic alcohol using 'simulated moving bed chromatography'.

Mechanism Mar. 16, 2013

Solution after the jump!