I’ve long wanted to write something about maocrystal V total synthesis, but I’ve always been too busy around the time that people have completed it to get a blog post out reasonably close to the event. Fortunately, two back-to-back syntheses from the Zakarian and Thomson groups were published in J. Am. Chem. Soc. earlier this month and I’ve now got plenty time to write about both of them, starting with that of the Thomson group in this post.
I'd initially planned to write about the most recent 2 (or possibly all 3) syntheses in an epic all-in-one comparison blog-post, but in the interests of keeping these musings short and somewhat readable I've decided to break things down a bit. This week's installment will cover Sorenson's awesome synthesis from back in April.
As the name implies, crotogoudin is another natural product from the goldmine of bioactive compounds that is the Croton genus of flowering trees. Seeds of these plants have been used for hundreds of years to produce the famous , a violent emetic and purgative used in early medicine across the globe before anyone realised just how bad it really was. Now, the notorious extract is mostly used as a source of various natural products, a reproducible way of inducing pain and/or irritation in animal experiments and a case in point that things described as 100% natural can still be extremely bad for you. It also serves as the major source of the important natural product , and gave its name to crotonic and tiglic acid (and thus crotonaldehyde). Along with a number of other natural products isolated from this genus, crotogoudin displays promising cytotoxic activity, which, coupled with the rare 3,4-seco atisane skeleton, was probably one of the reasons that the Carreira group recently embarked on its total synthesis.
That's right, for the first time in three and a half years' blogging I find myself writing about that rarest of publications: the collaborative total synthesis. Also somewhat unusually, the two US-based groups involved in the collaboration are both headed up by professors who originally hail from outside the States.
Paul Dochety's blog at 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 (think British C&EN, if you're not familiar with it). However, his tenure there has recently also , 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 , authorship will be shared between myself, Karl Collins (of ) and the legendary Chemjobber (anyone who needs a should really rethink their blog-reading priorities).
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!