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Articles Archive for February 2009

Still In The RBF »

[28 Feb 2009 | 21 Comments | 17,150 views]
Sporolide B

Nicolaou, Tang, Wang. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900264.
The second of two papers published (almost) in succession in Angewandte from the KCN labs (also check out some more methodology in JACS – nice to see more methods from his group), sporolide B is the more challenging target, but devoid of any biological activity.  Nicolaou justifies his synthesis by discussing the biosynthetic origins of the sporolides, which are potentially products of enediyne cyclisation.  Convinced?  Perhaps…
Anyway, the structure is certainly interesting, being one of relatively few natural products that …

Methods, Still In The RBF »

[25 Feb 2009 | 14 Comments | 14,758 views]
BE-43472B

Nicolaou, Lim, Becker. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200900058.
Huh; you wait months for a Nicolaou synthesis, and then two come at once!  This little beastie and sporolide B dropped in Angewandte on consecutive days, both represented by abstracts drawn in the now familiar crayon-o-vision styling of La Jolla’s most-prolific chemist and photoshop abuser. Seriously, check this stuff out – this is on his home page!  The last time I saw anything like this I’d been over-doing both the ether and the geocities…

Of course, all this wouldn’t be …

Still In The RBF »

[22 Feb 2009 | 5 Comments | 9,186 views]
Norhalichondrin B Pt. II

Phillips, Jackson, Henderson, Motoyoshi. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200806111.
I kinda ran out of steam whilst writing the first post on this synthesis, so I stopped basically after the fragment synthesis was complete.  So now it’s time to finish the synthesis, putting the finishing touches to enormous target.  Phillips’ strategy was to assemble the macrolactone first, then append the LHS polyketal, using cross metathesis to stitch the two main fragments together.  The article contains a couple of errors in the caption for this reaction; numbered reagents are …

Editorial »

[21 Feb 2009 | 3 Comments | 12,000 views]
Some links, and yes, Hexacyclinol…

I’ve been sent a pair of links to pass on to the chemical community:
1. I saw that not all your posts are total syntheses and that publication is a bit slow so I thought I’d suggest you mention ChemTube3D  http://www.chemtube3d.com to your readership who I am sure would enjoy it. It is a free site.

I hope you are already familiar with the site, but if not, you can read some background in the “press release” I prepared for Chem Eng News Digital Briefs.
Nick Greeves [co-author of The Big Green Book of Organic Joy]
Director of …

Still In The RBF »

[16 Feb 2009 | 17 Comments | 12,335 views]
Norhalichondrin B Pt. I

Phillips, Jackson, Henderson, Motoyoshi. ACIEE, 2009, EarlyView. DOI: 10.1002/anie.200806111. Article PDF Supporting Information Group Website

As I said in the last post, it was a rather quiet fortnight for total synthesis, at least as the big journals go. However, I think Andy Phillips can feel justified in his absence when he’s been cooking molecules like this ‘un up. Norhalichondrin B is part of the halichondrin family, isolated about twenty years ago – plenty of time for a bit of synthetic action, kicked off by Kishi back in ’92. Impressively, the synthesis hasn’t been entirely academic, with the peeps at Eisai Pharma also working on analogues. So how to start (lots of grant-application forms…)?

Methods, Still In The RBF »

[10 Feb 2009 | 25 Comments | 14,115 views]
Spirangien A

Paterson, Findlay and Noti. Chem. Asian J., 2009, ASAP. DOI: 10.1002/asia.200800445. Article PDF Supporting Information Group Website

It’s been a rather slow week in the world of total synthesis – I normally have a check on the ASAPs and EarlyViews in JACS and Angewandte every day in Google Reader (BTW, tune directly into my brainwaves under the ‘What I’m Reading’ section on the right…), and a bit less often, I’ll read Org. Lett., Chem. Comm. and OBC. If nothing turns up, then it’s on to Chem. Eur. J, JOC, and maybe even Tetrahedron… but today I took a far eastern excursion and found this distinctly Scottish paper (66% at least…). The thoughts going through my mind at this point were firstly, 1. I recognise that structure, 2. Ah, it’s Ian… 3. …and Alison – a former housemate from when I was living in Cambridge. It wasn’t just a house we shared, though – we also shared group meetings, and I remember this strucuture coming up, as Alison had just finished Dolastatin (that’s some old-school TotSyn right there…). I actually found the pentaene moiety the more interesting chunk, but of couse Ian Paterson’s all about the aldol.

Still In The RBF »

[2 Feb 2009 | 29 Comments | 16,706 views]
Valerenic Acid

Mulzer and Ramharter.  Org. Lett., 2009, ASAP. DOI: 10.1021/ol9000137. 
Mulzer’s1 work is starting to form a theme, at least in my mind, of small, complex and (mostly) highly oxidised natural products, made with whatever tools are most appropriate, rather than shoe-horning in methodology.  He also seems to work his students individually, or in small teams – not unlike my schooling, and one that I certainly appreciated.  Today’s synthesis is that of a GABA receptor modulator, valerenic acid.  For the uninitiated, the GABA receptor (?-aminobutyric acid) is a key component in neurotransmittion, but has …

Chemistry World, Still In The RBF »

[1 Feb 2009 | 10 Comments | 8,184 views]
Chemistry World: Penifulvin A

Latest piece for the RSC in the February issue of Chemistry World