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 …

Sarpong, Fischer. JACS, 2010, 132, 5926 DOI: 10.1021/ja101893b.
It’s quite hard to explain the phenomenon of simultaneous publication to people outside of chemistry, ’cause it simply isn’t easy to rationalise.  This is now twice in as many months, as Englerin A took my fancy in this month’s Chemistry World.  I’ve never been in the situation of working on a target with rival groups bearing down on me, but it must be quite punishing (I took the slightly easier option of working on a target that 1. had …

Bradshaw, Bonjoch, Etxebarria-Jard?´. JACS, 2010, ASAP. DOI: 10.1021/ja101994q.
It’s been a while since I wrote about a synthesis from Spain, so it’s nice to return with a rather sweet synthesis from the labs of Josep Bonjoch and his compatriot, Ben Bradshaw. Their efforts have been focused towards a sub-set of diterpenoids produced by Aspergillus, in which the decalin ring junction contains a pair of quaternary carbons.  That’s a pretty significant challenge by itself, but the rest of the decalin in subsituted in an all cis- arrangement, making for …

Apologies for the lack of blogging, friends.  This has in part been due to a lack of free time, but also to my computer going BANG.  A wisp of smoke and an horrendous smell indicate a ‘knackered’ power supply, so it’s going to be a little while longer before I’m back in action again. In the mean time, do read my CW article from last month – Polycavernoside A.  No surprises for guessing what next months CW piece will be – those intreguingly similar publications of Englerin A (one and …

Overman, Martin, Rohde. JACS, 2010, ASAP. DOI: 10.1021/ja100178u.
I don’t think there is a single academic whose syntheses I look forward to more than Larry Overman.  I’m not sure exactly why that it, but I think the main reason is the overall standard of his work, as well as his tendency to write fascinating and informing full-papers.  He’s also one of those professors who ‘owns’ a particular type of natural product; ‘Overman molecules’ are of course, alkaloids.
This paper not only discusses a ‘first synthesis’ in a racemic form, but also a …