B.R.S.M. Yield isn't everything

29Jan/141

Chemistry World: Organic Matter

Organic Matter_beige_300

Fantastic artwork from the RSC

Paul Dochety's blog at Totallysynthetic.com was a massive inspiration to me in my early days as a blogger, showing me that there was enough of a synthetic organic chemistry community online to make writing seemingly very esoteric posts on a small, specialised sub-field rewarding and worthwhile. A couple of years ago, Paul moved away from the online community, but continued his excellent monthly column for the RSC's Chemistry World (think British C&EN, if you're not familiar with it). However, his tenure there has recently also come to an end, and to try to fill the organic-shaped hole in its opinion pages the RSC has commisioned a new column – Organic Matter. As you've probably heard already, authorship will be shared between myself, Karl Collins (of A Retrosynthetic Life) and the legendary Chemjobber (anyone who needs a link to CJ should really rethink their blog-reading priorities). Karl was up first in the January issue, with this piece on some recent C-H oxidation chemistry, and I'm pleased to announce that my contribution to January's issue is now available online for free here. I'm super excited to be given this opportunity to be a part of the Chemistry World team and share authorship with two awesome chemists—and to see what Chemjobber gets up to in March!

Finally, I would like to wish Paul all the best; although unfortunately we've never made it past two degrees of separation, if I'd never read  Tot. Syn. I would not have started this blog, and would never have considered writing or publishing as possible career moves. Thanks, man!

 

Filed under: Total Synthesis | 26,438 views | 1 comment 1 Comment
20Jan/1425

The Best Thing Ever?

This week’s group meeting’s talk on ‘Strategies in Synthetic Planning’ raised a number of interesting points for discussion, but I wanted to put just one to my readers and the online synthetic community: what’s your favourite total synthesis?

Strangely, the question actually put to the group was a bit less subjective—the word "best" was used, as if there's a single right answer—but I've found that whenever conversations along these lines occur, that there's a wide spectrum of answers. The history of total synthesis—while rather short compared to many branches of science—is still vast, and there’s a lot of great work out there that I'm not sure can (or should) be ranked on some absolute scale. One problem is that there are just too many criteria on which syntheses can be judged (length, creativity, yield, scalability...); although I’ve heard several people liken completing a total synthesis to running a marathon, there’s much more to it than just doing it fast! I remember Rob Stockman introducing Andrew Phillips while chairing a session at a conference a few years ago by comparing the styles of different synthetic chemists to those of different painters, and I think that the analogy is a good one.[1] Looking back across the body of work produced by the synthetic community it’s easy to identify the “old masters”, but few would be prepared to rank them in order of greatness; you’d just as well choose a "best" fruit or colour.[2] Sure, there are now a bunch of metrics for assessing synthesis on everything from atom economy to percentage ideality,[3] but I’m pretty sure that’s not how K. C. Nicolaou decided what to put in his Classics in Total Synthesis series and I think it’ll be a while before we see a really elegant route to a target designed by a computer.

Anyway, that’s probably enough pontification for one blog post, so here are a few of my favourite syntheses and a few that came up in recent conversations—please add yours and your thoughts in the comments!

Filed under: Ask the audience, Current Literature | 56,084 views | 25 comments Continue reading