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Articles Archive for August 2008

Still In The RBF »

[31 Aug 2008 | 49 Comments | 19,057 views]

Du Bois and Mulcahy. JACS, 2008, ASAP. DOI: 10.1021/ja805651g.
One quick inspection, and you know we’re looking at a dinoflagellate neurotoxin, with more guanidine groups and derivatives than you can shake a stick at.  Unlike other large families of natural products with common functionalities, there doesn’t seem to be a universal strategy that (whilst ugly) could synthesise the majority of the family.  This means we get to see a whole variety of strategies towards these targets (and ultimately, the daddy, palau’amine).
Du Bois’ approach starts with the use of …

Still In The RBF »

[26 Aug 2008 | 6 Comments | 7,536 views]

Panek and Lowe. Org. Lett, 2008, ASAP. DOI: 10.1021/ol801499s.
More of a progress update than anything else, this paper, along with a previous report (DOI: 10.1021/ol0501875 ) detail an interesting synthesis of Kendomycin.  I say progress update, as the synthesis plan was outlined in the latter paper, but it’s always nice to see a plan come together.
As is often the case, the bulk of the paper can be summarised in a (somewhat cluttered) retrosynthesis.  Much of the C9-C20 portion in built using relatively well known chemistry, …

Still In The RBF »

[17 Aug 2008 | 56 Comments | 41,396 views]

Nicolaou, Chen, Sun, Peng and Polet. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200803550.
A second showing for this natural product on these pages, the first synthesis was by a former student of Nicolaou, Phil Baran, three months ago.  However, this is quite a different piece of work, as Nicolaou completes the synthesis from scratch – whereas the Baran approach was more a semi-synthesis.  I covered the (few) biological detail in the previous post, so we’ll move on to the synthetic action directly.
Now, I said that Nicolaou started the …

Still In The RBF »

[16 Aug 2008 | 10 Comments | 9,115 views]

Barrett, Soorukram and Qu. Org. Lett, 2008, ASAP. DOI: 10.1021/ol8015435.
This is the second example of Barrett’s benzyne centred three-component-coupling I’ve featured on the blog, and it’s still looking like a damned smart way of constructing heavily substituted aromatic systems.  The first was ent-clavilactone B, back in 2006, which shares a further couple feature with todays target – lack of an established absolute stereochemistry, and bacteria-bashing activity.  For those that didn’t cover benzynes in their schooling, there’s one key feature of their reactivity that is key to …

Still In The RBF »

[13 Aug 2008 | 16 Comments | 10,941 views]

Trauner, Andersen, Volgraf, Lumb, Brastianos, Carr, Chung, Münzel and Mauk. Nat. Chem. Bio., 2008, ASAP. DOI: 10.1038/nchembio.107.
Starting to look like the king of biomimetic synthesis, Dirk Trauner (soon to be moving to Munich – the TUM I believe LMU – I stand sit corrected) has dropped the synthesis of another polyaromatic beast, this time into Nature Chem. Bio.  This isn’t too uncommon – Kozmin showed his take on Leucascandrolide earlier this year (though I’m bored to tears with that macrolide).  Although there is a degree …

Still In The RBF »

[7 Aug 2008 | 4 Comments | 5,892 views]

Overman, Nilsson, Read de Alaniz and Rohde. JACS, 2008, ASAP. DOI: 10.1021/ja804624u.
As pointed out in the comments by some of the ‘yoof’ readership ‘The man [Overman] totally owns alkaloids'; indeed, this is definitely an Overman-type target.  The target(s) have been through a couple of postulated structure variations, so the group wasn’t entirely sure what the actual configuration of the spiro centre was.  However, the smart money was on the configuration shown (and borne out in this synthesis).
Biological profiling of this small family has been distinctly limited.  …

Chemistry World, Still In The RBF »

[5 Aug 2008 | 3 Comments | 5,728 views]

Latest piece for the RSC in the August issue of Chemistry World…

Still In The RBF »

[4 Aug 2008 | 10 Comments | 7,180 views]

Hashimoto, Nakamura and Kikuchi. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200802729. Hashimoto, Nakamura, Inagaki, Sugimoto, Kudo, Nakajima. Org Lett, 2001, EarlyView. DOI: 10.1021/ol0168364.
A second synthesis of this beast (the first being Zakarians) and, it’s not looking any less complex.  I had a look back at the Zakarian post, and I was surprised to see that I didn’t mention any biological activity.  However, Hashimoto and Nakamura only mention ‘…reported to activate Ca2+ channels…’, so I guess that counts as a reason to make more and discover what …

Still In The RBF »

[1 Aug 2008 | 56 Comments | 33,067 views]

Baran and Newhouse. JACS, 2008, ASAP. DOI: 10.1021/ja8042307.
This was one of the final presentations at the BOSS conference (which I’ve still not finished blogging), discussed as part of Baran’s impressive talk.  We can leap into the chemistry pretty quickly, as Baran pointed out in his lecture that there’s no biological activity. (However, I bet it does something.  Give it a go, Tim – you’ve got 2.5g going spare – try some in a nice strawberry and banana smoothie and get back to us…)1

So for the first …