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Articles Archive for January 2009

Editorial, Methods »

[29 Jan 2009 | 36 Comments | 15,976 views]
Abstract Graphics

It really is time that someone took the crayons away from KCN – the covers of the Classics books are bad enough without this crazy colouring-in competition turning up in JACS abstracts…
Also of note – nice work by Carreira in Nature today; this’ll be in my RSC Chemistry World column.

Still In The RBF »

[28 Jan 2009 | 25 Comments | 10,512 views]

Kerr and Carson. Org. Lett., 2009, ASAP. DOI: 10.1021/ol802870c.
After the ChemDraw marathon that was helicterin B, I was bloody glad to move on to a smaller target (even if the configurations are tightly packed…). This one has a pretty decent biological profile, and with a phosphate group hanging off it, no surprises that it interacts with the DNA machinary. I’m not going to blab on about it, but it’s certainly a worthy target; this’ll be why syntheses by Snider, Sorensen and Fukuyama (amongst others) are …

Still In The RBF »

[25 Jan 2009 | 37 Comments | 14,825 views]
Helicterin B, Helisorin, and Helisterculin A

Snyder and Kontes. JACS, 2009, ASAP. DOI: 10.1021/ja806865u.
It’s amazing how ideas arrive in pairs. Think: Deep Impact and Armageddon, or The Prestige and The Illusionist. Or bloody Peter Mandelson and Ken Clarke… And in as many weeks, we have Porco’s synthesis of chamaecypanone C and Synder’s synthesis of helicterin B, united through the key use of a retro-Diels-Alder/Diels-Alder cascade. The ‘why?’ in this case seems to be a shared love of dimeric (and tetrameric) natural products, where this kind of chemistry is a …

Still In The RBF »

[19 Jan 2009 | 20 Comments | 8,593 views]
Chamaecypanone C

Porco, Dong, Hamel, Bai, Covell, and Beutler. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200804883.
It’s not often I’m surprised by the origin of natural products, afterall ocean trenches, acidic pits and frozen wastelands have all revealed ‘tartan TLC-plates’, but I didn’t consider tree heartwoods as likely targets. On second thought, why not? Loads of trees yield interesting isolates, but there’s something about heartwood that makes me think ‘woody’, and not much else… I mean, I’m currently resting my forearms on a lump of beech – and I’ve never …

Still In The RBF »

[13 Jan 2009 | 18 Comments | 9,587 views]
Phorbasin C

Micalizio and Macklin. JACS, 2009, ASAP. DOI: 10.1021/ja809491b.
An interesting test-case for new methodology, this family of diterpenes has a pretty novel architecture. The unsaturated sidechain is the bit I find intreguing, as skipped-conjugation is tricky to keep that way. Oh, there’s some bio-stuff to provide a little rationale (including a bit of bacteria growth inhibition, and some cytotoxicty), but nothing startling. Micalizio is in it for the chemistry, and concern about the C-11 stereocenter, which was unassigned when they started their work…

As they didn’t …

Editorial »

[12 Jan 2009 | 5 Comments | 6,653 views]

Just a quick news-nugget before I get on with the real business of the day – phorbasin C – but even though the Hayashi synthesis of Tamiflu is super-sweet, it may be a waste of time.  There’s a slightly worrying article about it’s uselessness against the most prevalent USian strain of flu over at the NWTimes. The article goes on to suggest that GSK’s Relenza might be a better bet for now.  Now, any smart ideas? I can see a SAD, potentially a Knovenagel, and maybe an Evans Aldol…

Editorial »

[9 Jan 2009 | 5 Comments | 11,570 views]

A break in your usual programming for some blatant advertising. However, there’s some good stuff here:
i. ‘Hi Paul,
We talked several months ago about a chemistry dictionary I had developed for word processors.
I have completed a major upgrade to the chemistry dictionary with the help of chemspider.com. The dictionary now has ~140,000 words.
Read my write up about the dictionary and download the file here:
I think it will be valuable to you and your readers.

I think this is a cracking idea, and well done to both Adam Azman at UNC who …

Featured, Still In The RBF »

[4 Jan 2009 | 27 Comments | 17,273 views]
Oseltamivir (Tamiflu) Pt. 6

Hayashi, Ishikawa and Suzuki. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200804883.
It’s back! Not just Tot. Syn., reanimated refreshed after a decent winter break, but Tamiflu too (thanks to all those who flagged this one up for me. In this case, in a (marginally) different guise, as what we’ve got here is Oseltamivir-free base, not the phosphate salt normally isolated. Not an important fact, but the salt formation probably makes quite a difference in-vivo…
However, that doesn’t matter a damn when the synthesis is a sweet at this. …