#Retrotime - Cycloheximide

Cycloheximide 1 is a cheeky number that is worth a mention.  It is a tool compound with a proven track record of actually being useful, with its years of use in cellular biology.  Regarding retro, I have included a brief synthesis at the end, so no peeking as it will tarnish your retrosynthetic blank canvas.

Blockbuster - Atorvastatin

Most blogs appear to have a generic period of time, where the posts are as frequent as a British person winning Wimbledon.  To get the ball rolling (again) down the mountain of productivity, through the plain of peril to the crown of command, I am posting one of my first ideas for The Stirrer Bar.  I thought some aid memoires for drug molecules/tool compounds would be useful for translating molecular structures to biological functions etc. Queue wikipaste...

Beware non-benign alkyne

Alkynes will probably feature a lot in this blog due to their bioorthoganol nature – but beware, as a recent paper demonstrates, everything can change in the local environment of a protein.

The Peterson olefination

There are many different ways to synthesise alkenes in organic synthesis. The problem in many cases, especially those in macrocycles or non-cyclic systems is getting good E/Z selectivity. Several methods are possible however, one of the simplest is the peterson olefination. The reaction allows control of E/Z selectivity by the conditions used to remove the silane.  

Synthetic polymers self-assembling into catalytic structures

Modern organic chemists have access to a huge range of different chemical reactions and, these days, even the most complicated natural product could probably be synthesised if somebody wanted to. However, nature still does chemistry a hell of a lot better than even the best organic chemist; enzymes allow even the simplest organism to catalytically (and often asymmetrically) carry out organic reactions at room temperature in an aqueous environment. Being able an enzyme’s characteristics artificially would be, obviously, hugely advantageous. And there are a number of project on-going particularly using supramolecular chemistry, dendrimers or polymers. Another method, one of the first in a completely aqueous environment, has been described in a short communication in Angerwandte by the Palmans group. It utilises a simple polymer functionalised with L-proline allowing it to diastereoselectively catalyse an aldol reaction with cyclohexanone and p-nitrobenzaldehyde.

‘Arsenicals’

When I read the title of this paper – Arsenical-maleimide for the Generation of New Targeted Biochemical Reagents – I thought you’ve got to be kidding, but having perused the abstract, I realised that I had much to learn.

Quite interesting: Sodium bicarbonate

I suspect some people are reading that title thinking “really?” But the fact of the matter is that the synthesis of sodium bicarbonate was the first triumph of industrial chemistry and therefore the first entry of the private sector into the chemical arena, something that still sets chemistry apart from the other major academic sciences, biology and physics; this is one of the reasons that chemistry is so advanced today.

But why sodium bicarbonate, is it really that important? The obvious answer is yes, but for things that we all now take for granted; soap and white cotton shirts. If this still sounds weird the industrial synthesis of sodium bicaronbate was described in 1856 as “one of the great benefits, if not the greatest that modern science has bestowed on humanity” but why?