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Headline, Still In The RBF »

[22 Jan 2012 | 16 Comments | 30,620 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 …

Still In The RBF »

[17 Jun 2010 | 11 Comments | 12,150 views]
Fawcettimine

Jung, Chang, Org. Lett., 2010, ASAP DOI: 10.1021/ol1009762.
Although the number of actual steps in a formal synthesis is (or at least should be) smaller than in a full total-synthesis, I often feel that the actual work is harder.  Afterall, one is directly comparing ones work with that of another researcher, and in this case Michael Jung has got his work cut-out.  There aren’t many professors whose work is truly that daunting, but Clayton Heathcock is one of them. Jung’s work intercepts the Heathcock synthesis eight steps from then …

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[23 May 2010 | 4 Comments | 9,221 views]
Complanadine A part II

Siegel, Yuan, Chang, Axelrod, JACS, 2010, 132, 5924 DOI: 10.1021/ja101956x.
It’s finally time to examine the second synthesis of Complanadine A, and I have to say that this route couldn’t be further removed from the Sarpong synthesis.  Of course Siegel’s route takes advantage of the dimeric nature of the target, but it’d be more worrying if he didn’t.
The synthetic action begins with a rather nice alkylation. Starting with a unsymmetrical cyclohexanone, alkylation could have occurred on either (or both) sides of the carbonyl.  By using a sulfide, the deprotonation is …

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[6 Jul 2009 | 35 Comments | 22,531 views]
Haplophytine

Fukuyama, Tokuyam, Ueda, Satoh, Matsumoto, Sugimoto. ACIEE, 2009, ASAP. DOI: 10.1002/anie.200902192.
And it’s done.  It took almost as long to finish as it took Wiley to finally put it online (are they using dial-up modems?), but it’s finally here, after many (as yet) unsuccessful attempts [Corey, Padwa, Nicolaou].  Unfortunately, its difficult to know exactly what were the more challenging issues, as this is a very compact communication – we’re gonna have to wait even longer for the full paper.  However, we can marvel at the more obvious …

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[2 Jun 2009 | 24 Comments | 11,069 views]
Ricciocarpin A

List, Michrowska. Nature Chem., 2009, AOP. DOI: 10.1038/nchem.215.
Another rather short blog post, but why wax-lyrical when the synthesis is short and sweet?  Ben List is still hammering-away at his niche in organocatalysis, this time reporting a rather nice domino reaction.  The target of the synthesis is a isolate of a liverwort, and possesses “potent molluscicidal activity” – not a biological effect I’d come across before.  It turns out that this natural product spells doom for Biomphalaria glabrata water snails…  and we’re still at a loss.  Water …