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Articles Archive for September 2008

Still In The RBF »

[29 Sep 2008 | 25 Comments | 9,651 views]

Deslongchamps, Phoenix and Reddy. JACS, 2008, ASAP. DOI: 10.1021/ja805097s.
I’ve got that unsettled feeling that one sometimes gets after reading a paper, and not quite getting it.  I can’t put my finger on it, but there’s something that didn’t read right with this synthesis by Pierre Deslongchamps.  The problem is a lack of specifics in places, but we’ll get to that in a bit.  The natural product is quite interesting from a biological perspective, as it acts as an inhibitor of Na+,K+-ATPase, just like digitoxin.  However, it’s structure …

Still In The RBF »

[23 Sep 2008 | 65 Comments | 11,148 views]

Holmes, Macdonald,  Horsley,  Ryan and Saubern. Org Lett, 2008, ASAP. DOI: 10.1021/ol801604z.
I’m thoroughly glad I took a little more time to dig through ASAPs I’d missed, as I’d somehow neglected this Org Lett published by Andy Holmes.  Y’see, some of the work towards the natural product was conducted in the lab I started my PhD in, back in 2004 in Cambridge.1 However, I’ll leave the reminicing for later in this post.
The target, histrionicotoxin 285A, was (like the rest of the family) isolated by blending poison-arrow frogs, and …

Editorial »

[21 Sep 2008 | 3 Comments | 4,427 views]

Sorry, yet again, for the lack of posting.  But for once, it’s not entirely my fault.  I spent a good chunk of this evening reading Brian Stoltz’s full paper on the synthesis of alkaloids using enantioselective oxidation (resolution).  It’s great, but I covered it back in 2006 (synthesis of amurensinin).  Then I went through Amos Smith’s lyconadin A and B, but we looked at that last year.  Nicoloau has also been pumping out full papers to accompany earlier communications.  This is great – full papers are A Good Thing, but …

Still In The RBF »

[14 Sep 2008 | 36 Comments | 11,199 views]

Kerr and Leduc. ACIEE, 2008, EarlyView. DOI: 10.1002/anie.200803257.
We’ve not got much to go in terms of biological activity (GABA receptor antagonism by a diastereoisomer…), so lets just assume that we’re in it for the chemistry.  It’s quite a nice looking target, leaving me somewhat surprised that this is it’s first synthesis, so props to Michael Kerr for digging it out of the 1962 bag…
So, to the synthesis – and surprisingly to the very reaction, protection of butenol as it’s PMP ether.  They used a Mitsunobu reaction to …

Methods »

[9 Sep 2008 | Comments Off | 1,974 views]

P. A. Evans et al. Intermolecular rhodium-catalyzed [3+2+2] cyclization of alkenylidenecyclopropanes with acetylenes. 10.1021/ja803691p

Chemistry World, Still In The RBF »

[5 Sep 2008 | 22 Comments | 9,101 views]

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

Methods »

[2 Sep 2008 | Comments Off | 1,759 views]

P. Knochelet al. Aryl and heteroaryl indium reagents for Stille / Suzuki style coupling. 10.1002/anie.200802292

Methods »

[2 Sep 2008 | Comments Off | 2,489 views]

A. Nishida et al. Catalytic, asymmetric Danishefsky-type Diels−Alder reactions. 10.1021/ja804430n

Methods »

[2 Sep 2008 | Comments Off | 2,274 views]

Picked up by Dan @ Curly Arrow:
S.V. Ley et al. Primary Amides from Esters. 10.1021/ol801398z