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Articles Archive for February 2007

Still In The RBF »

[27 Feb 2007 | 8 Comments | 6,557 views]

Williams, Tsukamoto, Greshock and Grubbs. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200604378.
As suggested in the comments on a previous article (thanks, “tired by chemistry”!), this synthesis of these related compounds by Robert Williams and his group is really quite nice. We’ve already had a look at this family, back in June of last year, with Phil Baran’s synthesis of avrainvillamide and stephacidins A & B, and the relationship between the members of the family are reasonably well established, as is the biosynthesis. However, a recent report now brings the notoamides to this …

Fresh Meat »

[23 Feb 2007 | 18 Comments | 13,678 views]

Köck and Grube.  ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200604076.
An interesting debate has sprung up in the comments on this little beastie (thanks for the tip, folks!), as several groups around the world are working on palau’amine as a target. However, this Angewantde reports the isolation of a family member, tetrabromostyloguanidine, with different relative stereochemistry. Most interestingly, the deviation appears to be centred on the ring junction on the fused saturated 5,5 rings – with a trans ring junction in the newly isolated product. The NMR evidence in itself is convincing, and …

Still In The RBF »

[22 Feb 2007 | 8 Comments | 5,883 views]

Danishefsky and Sun-Joon Min. ACIEE, 2007, EarlyView. DOI: 10.1002/anie.200605058. Another top synthesis from the Danishefsky labs this month (is that four published this year so far? He must be cracking the whip!), this time of the biologically exciting terpeniod, paecilomycine A. The biological profile is well documented in the paper, but the headlines are 10 nM neurite outgrowth activity in PC12 cells, and significant nerve growth factor stimulation.

Their retro-synthesis is simplicity itself, using a intermolecular DA to construct the initial cyclohexane, then a Pauson-Khand to complete the decalin and fused …

Still In The RBF »

[19 Feb 2007 | 24 Comments | 7,478 views]

Denmark, Regens and Kobayashi. JACS, 2007, ASAP. DOI: 10.1021/ja070071z.

Definitely a target of split personalities, or at least lipophillicities, papulacandin D and the rest of the family represent an interesting synthetic challange, as well as a powerful antifungal treatment. The first and only synthesis of this natural product was completed by Tony Barrett, back in ’96, using not entirely different disconnection, but I guess that is no surprise. However, the implementation of the chemistry used by Denmark is quite a different beast, using his own chemistry twice, and in a …

Still In The RBF »

[11 Feb 2007 | 23 Comments | 11,114 views]

Deukjoon Kim, Kim, Lee, Lee and Kim. JACS, 2007, ASAP. DOI: 10.1021/ja068346i.
Continuing their fascination with natural products derived from the Laurencia family (not an uncommon fascination!), Deukjoon Kim’s group (the same team that brought you this post) has completed two more related structures, each with that eight-member ring, often found in the family. They base most of the work on an advanced intermediate, created in their synthesis of Laurencin (seven steps, 35% yield), containing that eight-membered ether ring, set for functionalisation.

The first step was halogenation, inverting the free hydroxyl; this …

Still In The RBF »

[4 Feb 2007 | 14 Comments | 6,606 views]

Ardisson, Lemos, Porée, Commerçon, Betzer and Pancrazi. ACIEE, 2006, EarlyView. DOI: 10.1002/anie.200604629.
Okay, so it’s been a pretty popular target, and the routes towards this potent beastie have been optimised to process-level perfection by Novartis, but its still a great way to show-off new technology. This is pretty much the approach taken by Ardisson’s group at Université de Cergy-Pontoise (which google maps informs me is just north-west of Paris), where they have used a unique aldol-type methodology to build this very aldol-friendly target.
For ill-prepared and initiated, disco(dermolide) is one hell of …

Editorial »

[1 Feb 2007 | 46 Comments | 8,114 views]

I received an interesting email from a chap at a top scientific publishing house, who is writing an article about chemistry and chemists in general. The gist of the email was that he’d like to know what we love about chemistry, and what we hate about it: “could [you] ask [your] readers to e-mail me if they’d like to comment on what they love or hate about working as a chemist”. Rather than publish emails on a blog, and end out flooding him with spam (I get over 200 spam …