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By W A Smit; A F Bochkov; R Caple; Royal Society of Chemistry (Great Britain)
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Additional resources for Organic synthesis : the science behind the art
Example text
This compound exhibited a wide range of antibiotic activity, but otherwise did not appear to be very promising from the point of view of medicinal utilization. As is quite common for fungal metabolites, no data were available about the role of 36 for the organism-producer. 11 of its structural peculiarity, ovalicin represented a challenging synthetic goal, a sort of testing ground to exercise the skills of organic chemists. Corey’s synthesis of racemic 36 in 198522awas undertaken merely as part of fundamental research aimed at investigating new synthetic methodologies.
Where n is the number of carbons in a molecule), Even for rather small organic molecules, quite a number of permutations are possible and thus the total number of generated structures might be truly astonomical. Consider, for example, compounds containing only 60 carbon atoms, a saturated aliphatic acids of general formula 70 in which the variable groups R' and R2can be located at any possible position along the chain. 21 group R' (or only R2), is If both groups are varied, the total number of possible structures will be x lo2' = a number greater, by a factor of lo7, than the number of atoms on our planet!
This route, while being generally applicable, is time consuming and requires a substantial amount of the compound to be degraded. In addition, in the course of the degradation, some structural information, especially that related to the stereochemistry of the broken bonds, will inevitably be lost. An independent synthesis is devoid of these shortcomings. The structure confirmed by this route can be considered to be an absolute truth no less than if established by a trustworthy Supreme Court. In many cases an independent synthesis turns out to be the only practical method to choose correctly between several tentative structures of an unknown compound.