Ma, Zi, Yu. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.201002299.
Why make one natural product when you can make two just as easily?  Or three in this case, but the headline syntheses are the Galbulimima Alkaloids GB-13 and GB-16 – notable members of a family that is getting some serious attention in pharma – one analogue is currently in phase III trials.  With all that potential, it’s not surprising that these beasties have seen quite a bit of synthetic attention; indeed, GB-13 was one of the first syntheses I …

Watanabe, Sumiya, Ishigami. ACIEE, 2010, EarlyView. DOI: 10.1002/anie.201002505. [No SI available]
As much as biological activity is a great rationale for working on a molecule, I do like it when a group does the chemistry for the chemistry.  To quote Watanabe, ‘Although urechitol A itself exhibited no biological activity, its unique tetracyclic structure prompted us to investigate its synthesis‘.  And when a group can make such an interesting molecule without too much resource, why not?  Key, of course, was building that fascinating cycloheptane, featuring not one, but two oxa-bridges.  Their plan was to …

This month’s Chemistry World column is Aplykurodinone 1, a rather neat Danishefsky synthesis.

Shair, Liau, JACS, 2010, ASAP DOI: 10.1021/ja104575h.
After wading through the Heathcock paper last week, I’m glad that today’s topic of discussion is a little shorter and easier to read.  (Seriously, part of me hates reading paper older that the 90′s as the style used in the schemes and figures is so difficult to follow.  Some of those 1960′s JACS papers are a real slog to get through – but worth it, normally….)
The target of choice today is Fastigiatine, a member of the Lycopodium alkaloid family, a popular …

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 …

Nicolaou, Chen, Kang, Ng, JACS, 2010, ASAP DOI: 10.1021/ja102927n.
Another popular target today; a last month I wrote a piece in Chemistry World about the first two syntheses of this target, and only a month later, up-pops Nicolau and Chen’s effort.  If nothing else, that’s a whole-lotta funding gone into this target, so it’s no surprise that it’s a pretty biologically active beastie. To quote KCN, ‘…potent and selective growth inhibitory (GI) activities against renal cancer cells‘ is the order of the day, so it’s worth all this effort. …

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 …