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Articles Archive for June 2008

Still In The RBF »

[29 Jun 2008 | 17 Comments | 8,968 views]

Leighton, Tran and Lombardi. Org. Lett., 2008, ASAP. DOI: 10.1021/ol8011869.
A nice little Org Lett, this; basically the story of one key transformation, but let’s look at the target first.  Manzacidin C would appear to have a fairly interesting biological profile, including α-adrenoceptor
blocking, but apparently there hasn’t been enough isolated to be able to assess this fully.  Ideal territory for a bit of total synthesis action, then – and there’s been quite a few.  There’s a good OBC paper reviewing the state of play as of the …

Still In The RBF »

[22 Jun 2008 | 70 Comments | 31,967 views]

Wang, Yang, Li, Gao, Tang, Dai, Wang. Org. Lett., 2008, ASAP. DOI: 10.1021/ol800977n.
Another top paper in from somewhere in China (there’s quite a few insitutions mentioned… and I got lost yet again trying to find a homepage… help?), this is certainly a different class of natural product, and one with quite a biological clout.  To quote the paper, we’re talking about ‘activity against B16 murine melanoma cells, the herpes simplex, and vesicular stomatitis viruses’ – a pretty diverse CV.  Hopefully you’ve all notice one intriguing structural feature …

Still In The RBF »

[18 Jun 2008 | 14 Comments | 6,538 views]

Corey and Surendra. JACS, 2008, ASAP. DOI: 10.1021/ja802730a.
Steroids!  Or at least something close to that structure.  This little beastie is actually classed as a ‘pentacyclic triterpenoid’ according to Corey, but it’s still a resolutely old-school target.  The synthesis is formal – what we’re targeting here is an intermediate in Johnson and Irelands synthesis way back in ’70.  That synthesis is definitely a tour de force, but somewhat lacking in efficiency with 32 steps.  Corey reckons that a biomimetic approach, stitching the ring systems together like …

Still In The RBF »

[9 Jun 2008 | 24 Comments | 14,160 views]

Zutter, Iding, Spurr and Wirz1. JOC, 2008, ASAP. DOI: 10.1021/jo800264d.
Again, I’m stretching that brief to include Tamiflu, basically because I find it such an interesting target. The more click-happy readers will have noticed that this paper comes to us from The Professionals at Roche, who make this bad-boy their business. And quite a synthesis it is too. Retrosynthetic analysis won’t get us anywhere here, so lets leap in with the forward.

Now that’s what I call a reduction! 5% Ru-Al2O3 with a …

Still In The RBF »

[2 Jun 2008 | 6 Comments | 5,423 views]

Bach and Selig. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200800693.
Another Overman target? I should think so; he completed back in ’89. But that doesn’t stop us mere mortals for following in his footsteps. Indeed, Bach seems to be snapping at them with this smart and original approach to this tightly functionalised natural product. There’s no mention of any biological activity in the paper, so let’s get on with the ‘synthetic challange’…
Bach kicks of with an astonishing pair of reactions to build the syn-6,5-fused …

Chemistry World, Still In The RBF »

[2 Jun 2008 | 16 Comments | 7,665 views]

As some of the more observant readers have already noticed, I’ve found myself a bit of ‘proper writing’ (it’s really weird to see my stream-of-conciousness in print!!!).  The folks at the RSC thought that little ‘ole Tot Syn was worthy of a monthly article in their Chemistry World publication, alongside Derek Lowe, Philip Ball and Dylan Stiles.  As I said in the comments, I’ll link to each article from here, but I won’t duplicate or rewrite that article, so you’ll have to make do for now!
The first one is on …