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Copying Nature in the Lab

October 12, 2000

Successful total synthesis of muricatetrocin -- a potential new cancer-fighting agent
Muricatetrocin is the name of a natural substance that may someday gain important victories
against certain cancers of the prostate, pancreas, and lungs. It was discovered in the leaves of
Rollina mucosa, a magnolia-like plant of the tropical rainforest, belonging to the custard-apple
family (Annonaceae). However, it is not possible to obtain large quantities of muricatetrocin from
this plant – no wonder researchers would like to reproduce this natural substance. Now there is
good news from Cambridge: a team of chemists working with Steven V. Ley can lay claim to the
first successful total synthesis of Muricatetrocin.
A total synthesis is considered to be the complete reproduction in the lab of a highly complex
substance isolated from plants or animals. In the past, the most prominent aspect of this was the
determination of the substance’s chemical structure. Now, thanks to efficient analytical methods,
this aspect has faded to the background. However, this elite field of organic synthesis is not less
important today. It is used to synthesize natural products, which could otherwise only be isolated
in tiny quantities, in amounts large enough to allow the investigation of their properties and
effects.
The first step on the road to total synthesis is a step backward, retrosynthesis: starting with
the target molecule, bonds are mentally taken apart, the molecule broken into pieces, in order to
find suitable, easily obtainable, inexpensive starting materials. These then have to react stepwise
to produce the desired structure in good yield, no easy undertaking. Natural products are usually
made up of a large number of asymetric carbon centers. These are the largest challenge in natural
products synthesis. If only one of these centers is present in the right-hand rather than the left-hand
form, for example, the result does not match the desired natural product.
„We will easily be able to vary the synthetic technique we have developed to produce
muricatetrocin in order to make related natural products accessible,“ says Ley. A highly
promising task, since this family of compounds, called acetogenins, includes a number of
biologically active products known for their activity against tumors, as well as bacteria, malaria,
and parasites.

Prof. Dr. S. V. Ley
Department of Chemistry
University of Cambridge
Lensfield Road
Cambridge, CB2 1EW
UK

Fax: (+44) 1223-336-442
E-mail: svl1000@cam.ac.uk

WILEY-VCH Verlag GmbH

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