Snyder, Tang, Gupta. JACS, 2009, 131, 5744. DOI: 10.1021/ja9014716.
Okay, it’s taken me far too long to get around to this article - I actually wrote the Chemdraw back when this article was in ASAP… but other stuff got in the way, like a little Nature paper from Baran. However, it’s a damned nice paper, so it’s impossible for me not to go back and look at it properly. The target here is an halogenated natural product, isolated from Streptomyces bacteria - so it’s not too surprising …
Barbas, Bui, Syed. JACS, 2009, ASAP. DOI: 10.1021/ja903520c.
Now, this is a bit of a fib already. I’m not entirely sure of Barbas’ reason for calling this paper a ‘formal total-synthesis of physostigimine’, as, whilst it is a formal synthesis, he actually stops at another natural product, esermethole. Now, this is fine - and it’s still a formal synthesis of physostigimine, but it is moreso a total synthesis of esermethole. Why he felt the need to call this a formal synthesis I don’t know.
It’s a shame …
List, Michrowska. Nature Chem., 2009, AOP. DOI: 10.1038/nchem.215.
Another rather short blog post, but why wax-lyrical when the synthesis is short and sweet? Ben List is still hammering-away at his niche in organocatalysis, this time reporting a rather nice domino reaction. The target of the synthesis is a isolate of a liverwort, and possesses “potent molluscicidal activity” - not a biological effect I’d come across before. It turns out that this natural product spells doom for Biomphalaria glabrata water snails… and we’re still at a loss. Water …
van Maarseveen, Hiemstra, Wanner, Boots, Eradus and de Gelder. Org. Lett., 2009, ASAP. DOI: 10.1021/ol900888e.
Okay, jsut a little Org. Lett. to get my hand back into this blogging thing after being on holiday for a week. The writing conditions have changed a little in Tot Syn towers, too - I’m now typing this on a new keyboard - a lovely aluminium Apple thing. So I bid my old Microsoft ‘Natural’ keyboard goodbye, after six years of faithful service, and also six years of crud (putting …
Davies, Williams, Schwartz, Denton, Lian. JACS, 2009, ASAP. DOI: 10.1021/ja9019484.
Now that’s a substituted ring… done and dusted by Huw Davies and Craig Williams as a collaborative effort (I’d quite like to know how this worked, as the two groups are quite removed), with Davies weighing in with some smart chemistry for building seven-membered rings. This clearly critical to the synthesis of such a molecule, but the challenge is the heavy substitution, which has thwarted several groups (including individual efforts). Whilst this paper doesn’t complete the …
Baran, Chen. Nature, 2009, AOP. DOI: 10.1038/nature08043.
They say that the best defence is a good offence, so I’m going to start latterly - and remind (somewhat forcefully, if necessary) all prospective commenters that the folks at Nature decreed that this paper is worthy. That’s good enough for me, so let’s avoid the tired arguments about suitability… </pre-emptive rant>
Anyway, what we’ve got here is typical of Baran - re-examination of chemical methodology of the past, and modernisation to solve problems in an orthogonal fashion. Breaking that down, …