New way of synthesizing organic chemicals mimics nature

July 15, 2011 by Lin Edwards report

Organic chemists have found a new way of synthesizing multiple complex organic molecules that until now have needed to be synthesized using time-consuming methods. The new strategy, which mimics natural biosynthesis methods, could provide a way to speed up the synthesis of chemicals for use in the laboratory and for testing for possible therapeutic effects.

Chemists can synthesize almost any complex organic chemical in small quantities in the laboratory, but the process can be extremely time consuming and expensive, and difficult or impossible to translate to large-scale production. It is also difficult to synthesize families or related molecules using traditional methods because each has to be synthesized individually.

The new method was developed by researchers from the Center for Catalysis at Princeton University in the U.S., led by organic chemist David MacMillan. The strategy combines two techniques that mimic methods used by living systems to synthesize organic molecules (those based on chains of or ): organocascade catalysis and collective . Combining these two techniques for the first time allowed MacMillan and colleagues to considerably speed up the synthesis of a group of six related .

The alkaloids the team manufactured were akuammicine, aspidospermidine, kopsanone, kopsinine, strychnine, and vincadifformine.

The new strategy, which the team calls “collective total synthesis,” makes it possible to synthesize useful amounts of related, complex molecules from a “common molecular scaffold,” and is much less time-consuming. The synthesis of strychnine, for example took place in only 12 stages, which is the shortest ever reported.

Traditional methods of synthesizing such chemicals have involved using chemical reactions to produce each individual intermediate and then isolating it and using the intermediate in the next reaction, and repeating this process until the target molecule is finally produced.

MacMillan said the new method represents a new way of thinking for organic chemists. Reducing the number of steps required to synthesize molecules reduces the time required and can also reduce the cost and wastage. Their approach can also produce a number of related molecules at the same time, which could reduce the time and cost of producing and testing chemicals to find the most bioactive drug candidates.

MacMillan and the team suggest the collective total synthesis strategy could be used to manufacture other families of molecules that until now have had to be synthesized individually. They say the approach of combining the two techniques of organocascade and collective synthesis could be applicable for many other groups of molecules besides alkaloids.

The paper, the first to be published describing this approach to synthesis, is published in Nature.

Explore further: Researchers simplify synthetic production of potential pharmaceuticals

Related Stories

Chemists synthesize herbal alkaloid

April 15, 2009

The club moss Lycopodium serratum is a creeping, flowerless plant used in homeopathic medicine to treat a wide variety of ailments. It contains a potent brew of alkaloids that have attracted considerable scientific and medical ...

Joining molecules together in Nobel matrimony

October 7, 2010

Three chemists who fundamentally changed the way we make everything from drugs to plastics to carbon-based electronics won the Nobel Prize in Chemistry for their work.

Recommended for you

A new form of real gold, almost as light as air

November 25, 2015

Researchers at ETH Zurich have created a new type of foam made of real gold. It is the lightest form ever produced of the precious metal: a thousand times lighter than its conventional form and yet it is nearly impossible ...

Moonlighting molecules: Finding new uses for old enzymes

November 27, 2015

A collaboration between the University of Cambridge and MedImmune, the global biologics research and development arm of AstraZeneca, has led researchers to identify a potentially significant new application for a well-known ...


Please sign in to add a comment. Registration is free, and takes less than a minute. Read more

Click here to reset your password.
Sign in to get notified via email when new comments are made.