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Headline, Still In The RBF »

[22 Jan 2012 | 16 Comments | 32,700 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 …

Featured, Still In The RBF »

[14 Jan 2012 | 33 Comments | 22,805 views]
Fusarisetin A

Li, Deng, Zhu, Lu, Yu. JACS, 2011, ASAP. DOI: 10.1038/nchem.1196  
Just take a quick look at that target and consider that the synthetic route I’m about to summarise took thirteen steps.  I’m fairly stunned – I read the top-line number in the abstract, and immediately thought that they must have started with an advanced intermediate or degredation product, but no – the synthetic action (like many natural product syntheses) begins with Citronellal.  Sure, only three of the rings are carbocyclic, but there’s a lot going on here, so lets get into …