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Articles Archive for July 2007

Still In The RBF »

[31 Jul 2007 | 18 Comments | 9,426 views]

Ley, Veitch, Beckmann, Burke, Boyer and Maslen. ACIEE, 2007, Early View. DOIs: 10.1002/anie.200703027, 10.1002/anie.200703028.
The completion of Azadirachtin, like Rapamycin (blogged back in December), marks the conclusion of a lengthy chapter in the Ley group, and having been a student at Cambridge for a few years, the progress on these molecules was frequently subject to rumour. It seemed that everyone knew someone who had worked on either, going back years to the early work. It must be very odd to have them complete, published and no longer a hot topic in …

Still In The RBF »

[24 Jul 2007 | 15 Comments | 4,977 views]

Yamamoto, Li and Payette. JACS, 2007, ASAP. DOI: 10.1021/ja073590a.
I know what you are thinking; not that f*cking molecule again! However, this approach by Yamamoto is really quite elegant, and contains some amazing transformations. I’m not going over the biology again – it’s all here: it would also be appropriate to point out this is a formal synthesis, heading for an intermediate found in other syntheses containing the challenging tetracyclic core. I’ve also not bothered with a retrosynthetic analysis (such a slacker, I know…), but their work differs from …

Still In The RBF »

[18 Jul 2007 | 36 Comments | 11,811 views]

Coldham, Burrell, White, Adams and Oram. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200701943.
Now this looks a little different from the past two syntheses: a nice pentacyclic alkaloid! Another difference is the brevity of the synthetic route: nine steps! When I saw the title, I was sure I’d seen a classic synthesis of the target, and this was confirmed with a reference to the Stork synthesis from 1963. In this paper a key tricyclic ketone was perpared in thirteen steps; in this work, Iain Coldham’s group manage this in six!
The key to this …

Still In The RBF »

[16 Jul 2007 | 43 Comments | 15,394 views]

Nicolaou, Chen, Guduru, Sun, and Banerji. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702243.
I didn’t manage the macrolide spectacular I promised in the last post, but here’s a gem I missed in the ASAPs from a few weeks back. The target is a landmark for several reasons, but the more aware of chemical politics will have noticed that this is the first (of many I imagine) publication from the Nicolaou/Chen labs at the A*star institute, Singapore. This venture is one that has captured a lot of interest, and I think many of us …

Still In The RBF »

[11 Jul 2007 | 9 Comments | 4,826 views]

Paterson, Ashton, Britton, Cecere, Chouraqui, Florence and Stafford. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200702178.
I think we’re going to do a bit of a macrolide spectacular this week, as there’s been quite a few publications of late. I’ve been privy to the progress on this molecule over the first two years of my Ph D, as our group shared meetings with the Paterson group. Therefore, I’d like to start by congratulating my colleagues back at Cambridge who worked on this impressive target: good job! The target has some interesting activity, as …

Still In The RBF »

[1 Jul 2007 | 64 Comments | 9,386 views]

Evans, Scheerer, Lawrence and Wang. JACS, 2007, ASAP. DOI: 10.1021/ja073590a.
The first JACS total synthesis I’ve seen in a while, this is a nice piece of work by the legend that is Dave Evans. The target certainly has a bit of a kick; I quote: “the most potent naturally occurring hallucinogen“. Interesting times for the students in that lab. I can see them now – being chased around the lab by malevolent HPLC machines… It’s apparently also the only non-alkaloidal psychoactive natural product, so certainly of quite some interest.
The …