A couple of weeks ago I attended a presentation given by Lisa Stowers from Scripps, entitled “Decision-making in the nose: a molecular rationale for the unpredictable nature of female behavior”. The catchy title did its job, so I was there, learning that reaction of female mice on male pheromones depends on (suprise-surprise!) phase of their estrous cycle. The neurobiology behind it is quite amazing, definitely worth reading about. However, my interest was triggered by one question asked after the presentation.
Kawamura et al. (Baran lab, Nature)
A paper with a very straightforward title, “Nineteen-step total synthesis of (+)-phorbol” (neither “concise”, nor “efficient”, “elegant” nor any other vague adjective) was published by Baran lab.
The step that impressed me the most was oxidation of compound 7. Chemo-, regio-, and stereoselectivity of this reaction was “easily predictable based on 100 years of C–H oxidation literature”, according to follow-up blog post, but I wonder how many chemists in the world would bet for this reaction to work so cleanly. Before reading the publication, of course.
Koh et al. (Hoveyda lab, Nature)
Expanding horizons of the metathesis reaction, Hoveyda lab teamed up with Schrock and developed a new catalyst and synthetic methodology for terminal Z-haloalkenes.
Battilocchio, Feist et al (Nat Chem)
Remember Morken reaction? I was daydreaming about streamlining it into bond-by-bond stitching of complex compounds. Turns out that Steven Ley was looking in the same direction, although through slightly different chemistry.
Yang et al. (Org Lett)
A nice example of ‘molecular gymnastics’ (proposed mechanism is quite a funny thing). Heads up from amphoteros blog.
Potter et al (JOC)
Safety first! Opt for hydrosulfate salt next time you prepare a diazotransfer reagent. I didn’t have problems with hydrochloride before, but will better give a try to hydrosulfate.
Adamo et al (Science)
…but hurry up with your diazotransfer, otherwise machines will soon do it for you! A fridge-sized synthesizer of known pharmaceuticals was constructed by chemists and engineers in MIT. Check out more detailed (and realistic) coverage by Derek Lowe.