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Articles Archive for June 2007

Still In The RBF »

[27 Jun 2007 | 20 Comments | 16,508 views]

Trost, and Stiles. Org. Lett., 2007, ASAP. DOI: 10.1021/ol070971k.
He’s done it :). Those of us who read Tenderbutton from the start will have known of Dylan’s work on this tasty little number, and he’s done it proud. Eight steps to the natural product; we’ll start with step one (or rather, the first non-literature step):

We’ve looked at Otera’s catalyst before, but as a quick reminder, it’s a funky trans-esterification catalyst. It’s been known for a little while, and the mechanism is in this JOC article. Nice to see it …

Still In The RBF »

[23 Jun 2007 | 11 Comments | 6,758 views]

Danishefsky, Krauss and Mandal. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200701837.
Yes, it’s another macrolactone, but this one’s a bit special, and there’s not an aldol in sight! Danishevsky and his group have been working with the Migrastatins for some time now, and have made several analogues, promoting that impressive cell-migration-busting activity. However, an isomer, the snappily and originally titled Isomigrastatin, has also been isolated, and Danishefsky quickly set to work.
I guess it’s no real surprise that that one of the key reactions was a diastereoselective Diels Alder reaction, and even less surprising …

Still In The RBF »

[18 Jun 2007 | 15 Comments | 8,019 views]

Grainger and Welsh. ACIEE, 2007, Early View. DOI: 10.1002/anie.200701055.
I’ll apologise immediately for overlooking this paper; last week was a little busy – I’ve been teaching myself the art of the Evans Aldol. I guess another reason I didn’t blog this paper is the deceptive simplicity of the target. Only two stereocentre; how difficult can that be. Look closer, and you notice the quaternary centre and the stereodefined tertiary amine, and it starts getting a bit more complex…

So how did they start? With a little induction of stereochemistry from …

Still In The RBF »

[7 Jun 2007 | 34 Comments | 10,361 views]

Evans, Kværnø, Mulder, Raymer, Dunn, Beauchemin, Olhava, Juhl, Kagechika and Favor. ACIEE, 2007, Early View. DOIs: 10.1002/anie.200701515, 10.1002/anie.200701520.
I promised it, and here it is – one damn impressive synthesis. I guess I should talk about it a bit, rather than just concluding with my introductory statement, so we’ll start with the biochemistry. The activity of the beast in humans is actually quite well known; it’s a potent poison, and there have been quite a few cases of azaspiracid poisoning documented. Of course, this isn’t the first synthesis of …

Still In The RBF »

[7 Jun 2007 | 8 Comments | 10,282 views]

Off-topic, yet again…
Some of you may have noticed that I’m interested in graphic design, and whilst I couldn’t design my way out of a wet paper bag, I still appreciate good quality work. A subset of that interest is in information mapping; basically, the was we represent data and the relationships between points, sets and groups. Some amazing work has been done by Columbia University’s W. Bradford Paley, Kevin Boyack and Dick Klavans, mapping scientific citations. The circular nodes represent a research area, and lines connect any nodes that contain …

Still In The RBF »

[5 Jun 2007 | 18 Comments | 9,718 views]

The legendary Tenderbuttoner just sent me an intriguing email, and I must interupt my blogging of Azaspriacid to let you all in:
Greetings. In the absence of my little tenderbutton.com I have no outlet for my random chemistry-related projects, so I’m reaching out to the rest of the chembloggers on this one. I’m advertising my latest scheme to take over the world, a DIY procedure to isolate pure nepetalactone, the active ingredient in catnip, using only itemsfound around the house. Soon every enterprising individual in the world will be commanding their …

Still In The RBF »

[3 Jun 2007 | 31 Comments | 14,377 views]

Ley, Andrews, Ball, Wierschem, Cleator, Oliver, Högenauer, Simic, Antonello, Hünger and Smith. Chem. Eur. J., 2007, Early View. DOI: 10.1002/chem.200700302; PNAS, 2004, 101, 12073-12078. DOI: 10.1073/pnas.0403300101.
Yep, I’ve finally got this one together, after much procrastination, and a mild leukascandolide diversion. Anyway, many of you will have seen the PNAS article from back in 2004; however, this is the real deal – a full paper on the synthesis of five Thapsigargins. The biological activity is discussed in quite some detail, explaining that the first use of this family in …