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Articles Archive for October 2008

Still In The RBF »

[26 Oct 2008 | 31 Comments | 14,352 views]

Canesi, Sabot and Berard. Org. Lett., 2008, 10(20), 4629-4632. DOI: 10.1021/ol801921d.
I nearly missed this paper, published online at the beginning of last month, but it’s an incredibly neat solution for the synthesis of some funky little natural products.  The parent molecule, panacene, has some fairly unique biological properties, as it is a shark-antifeedant.  In otherwords, it puts sharks of their food, and makes the sea-hare in which it is produced that little bit less attractive to the peckish big-fish.  Okay, so it doesn’t cure cancer, but the …

Still In The RBF »

[21 Oct 2008 | 14 Comments | 7,456 views]

Feldman and Fodor. JACS, 2008, ASAP. DOI: 10.1021/ja807020d. JOC, 2007, 72(21), 8076-8086. DOI: 10.1021/ja807020d.
This one looks, at least from the JACS communication, to be short piece of work over only two pages, but it’s very reliant upon methodology and ideas presented in a JOC full-paper from back in 2007, so perhaps we be best to read that one first.  Although this synthesis is racemic, that isn’t actually an important issue, as the natural product may be racemic itself.  The lack of certainty seems a bit …

Still In The RBF »

[16 Oct 2008 | 44 Comments | 13,391 views]

Nicolaou, Dalby, and Majumder. JACS, 2008, ASAP. DOI: 10.1021/ja806176w.
Not just a natural product in it’s own right, aspidophytine is a building block on the way towards haplophytine, quite a beast of a natural product.  You can read more about it in a Corey paper from two years back.  Aspidophytine is one half of the larger target, with Nicolaou’s approach towards the other half published last year, so it can’t be long until we see the finished product.  But let’s look at this fairly short paper first.
It’s basically …

Methods »

[14 Oct 2008 | Comments Off | 2,535 views]

K. A. Woerpel et al. Mechanisms for nucleophilic substitutions of cyclic acetals: nucleophile strength versus stereoselectivity. 10.1021/ol8019956

Still In The RBF »

[13 Oct 2008 | 10 Comments | 7,888 views]

Phillips and Griggs. Org. Lett., 2008, ASAP. DOI: 10.1021/ol802041c.
I guess Andy Phillips has been a rather busy-boy – not many researchers get back-to-back articles in Tot. Syn.!  However, both papers are definately worth writing about; his pyranicin synthesis showcases some rather neat methodology.  From a biological perspective pyranicin is fairly interesting, as it exhibits the same nano-gram ED50 values against a variety of cancer cell-lines as the more complex acetogenins.  Phillips suggests that it was this activity, along with inhibition of electron transport, that prompted their synthetic …

Still In The RBF »

[7 Oct 2008 | 28 Comments | 10,434 views]

Phillips and Henderson. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200803593.
Look familiar at all?  If you’ve seen Phillips’ synthesis of cylindramide A (back in 2005), you might have a strong feeling of déjà vu, but I didn’t cover it, so this is a good opportunity to look at Phillips’ work on this intreuguing class of natural products (termed the ‘tetramic acid containing macrolactams’).  Again, we’re short on biological data; just a quick mention of ‘cytotoxicity, antimicrobial activity, and the inhibition of superoxide
generation’, but not specifically for this molecule.  However, we’re …

Chemistry World, Still In The RBF »

[6 Oct 2008 | 13 Comments | 6,421 views]

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