[22 Jan 2012 | 16 Comments | 29,211 views]
Stenine Pt. 2

Zhang, Chen, Chen, Xie. ACIEE, 2011, 51, 1024. DOI: 10.1002/anie.201106587  
Second time around for Stenine on TotallySynthetic - the first synthesis I blogged takes us back to 2008, and Aube’s neat work focusing around a tandem Diels-Alder / Schmidt reaction. This latest publication moves the research to Kunming, China, the home of it’s use as part of Chinese herbal medicine.  That doesn’t alter the core of the synthetic strategy, though, as Hongbin Zhang seems to agree with Aube that building the cyclohexane core first is the key to this target.
Zhang, however, prefers the use of a …

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Editorial »

[18 Sep 2011 | 32 Comments | 23,049 views]
An Egotistical Diatribe

One of the most impressive results of sharing thoughts on the internet the speed of insight – it doesn’t take long for two and two to bump together neatly. Last year, some bright sods noticed that I’d changed my by-line in my Chemistry World column. When once it said “Paul Docherty is a medicinal chemist based in London, UK”, it now reads “Paul Docherty is a science writer and blogger based in London, UK”. With my Facebook, Linked-In and Google+ accounts reflecting the change in more detail, it’s not surprising …

Still In The RBF »

[4 Sep 2011 | 64 Comments | 20,628 views]
Maoecrystal Z

Reisman, Cha, Yeoman. J. Am. Chem. Soc, 2011, ASAP. DOI: 10.1021/ja2073356 
A busy couple of weeks in the Reisman lab, it appears – really nice syntheses of the Cepharatines and 8-Demethoxyrunanine in Angewandte (doi: 10.1002/anie.201104487), but I decided to blog this tasty synthesis of Maoecrystal Z.  Of course, this isn’t the first member of that family that I’e blogged – the seminal synthesis of Maoecrystal V made my December 2010 column in Chemistry World.  I remember when I wrote that piece that the pseudo-3D structure used to represent the target annoyed …

Still In The RBF »

[14 Aug 2011 | 19 Comments | 16,157 views]
N-Methylwelwitindolinone C

Garg, Huters, Quasdorf, Styduhar. JACS, 2011, ASAP. DOI: 10.1021/ja206538k
Technically beaten to the finish-line by Rawal (JACS in March), but still the first asymmetric synthesis of the Welwitindolinone family, this synthesis is one of many contributing to a hell of a year for Neil Garg.  I think the key to the synthesis was picking the perfect starting point – and dealing with poor yields that get you seriously further forwards.
That critical starting point is  fantastically smelling (S)-Carvone.  Not only does this make the lab (and presumably the chemist, his notebook, …

Guest Post, Still In The RBF »

[6 Aug 2011 | 17 Comments | 14,612 views]
Omphadiol

Romo, Liu. ACIEE, 2011, 50, 7537-7540. DOI: 10.1002/anie.201102289
Guest Blogger: SPF
What if I’d ask you to synthesize this little molecule with six neighbouring stereocenters from biologically available material? Oh, by the way you can’t use any protecting groups and keep it short! Sounds impossible? Not according to Romo et al.. They’ve achieved the synthesis of this stereo-dense molecule in 10 steps from (R)-carvone (Mmmhhh spearmint). (+)-Omphadiol belongs to the africanane (guess where they grow) family of sesquiterpenes. Its brothers and sisters show some significant bioactivity, but due to insufficient …

Guest Post, Still In The RBF »

[29 Jul 2011 | 10 Comments | 14,005 views]
Trigonoliimines A-C

Guest Blogger: See-Arr-Oh
Han and Movassaghi, JACS 2011, 10768-10771. DOI: 10.1021/ja204597k ; Qi, Bao, and Tambar, JACS 2011, 10050-10053. DOI: 10.1021/ja203960b .
It’s not too often JACS publishes total syntheses anymore, since their role as a general chemistry journal means every newly built molecule competes against quantum dots, in silico simulations,  or new battery materials. So you can imagine my utter shock and delight at finding not one, but two almost back-to-back syntheses in the past month!  First, the Porco / Ready combination of Kibdelone C, followed closely by two syntheses …

Still In The RBF »

[2 Jul 2011 | 23 Comments | 19,320 views]
Loline

Trauner, Cakmak, Mayer. Nat. Chem., 2011, 3, 543. DOI: 10.1038/nchem.1072
Simple tricyclic morpholine derivative with four stereocenters. Can’t take that much effort, can it? Well, yes it can – and it’s amazing how tricky this little beastie is! Trauner explains in the informative introduction that only one successful synthesis has been completed – taking twenty steps to get to the racemic target. Clearly that leaves the team in Germany with a lot of room for improvement.

The team made the first intermediate in the scheme …

Guest Post, Still In The RBF »

[16 Jun 2011 | 29 Comments | 18,385 views]
Cyanolide A Aglycon

Rychnovsky, Gesinski. JACS, 2011, ASAP. DOI: 10.1021/ja204228q
Guest Blogger: See-Arr-Oh
When I first saw the dimeric gamma-substituted pyran motif in this molecule, I said “Gotta be Rychnovsky” (or maybe Wender).   Throughout his career at UC-Irvine, Scott Rychnovsky has been the master of the TMS-promoted diastereoselective Prins cyclization, which he has applied to the synthesis of at least 10 macrolides.  Until now, however, none have been attempted sans protecting groups!
Cyanolide A was isolated in 2010, and it’s already been the target of four total syntheses.  Perhaps this is due to …