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By Jeremy J. Ramsden

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6 is generally much greater than in simple ketones such as acetone. 7. It is this delocalization of electrons that accounts for the presence of the enol form of 1,3-dicarbonyl compounds. 6, is a factor that also favours the enol tautomer. 8 Keto and enol tautomers. 3 .. 37 III III em 4a ll. vn One particularly well known organic reaction is the condensation reaction between 1,3-dicarbonyl compounds (which probably react as their enol tautomers) and aldehydes (the Knoevenagel reaction). In this reaction, a new carbon-carbon double bond is formed and water is produced.

Cyclic esters such as altemariol are called lactones. 16. 41 Ii III El El El El Alkylation Reduction Oxidation Decarboxylation Modifications to the carbon skeleton em 4a El ll. vn The structural variety of polyketide-derived natural products is increased enormously by secondary structural modifications. 3), in which an ester linkage has been created. The formation of these ester linkages can be considered as secondary modifications after cyclization of the polyketides has occurred. There are many types of secondary modification that can affect polyketide-derived natural products.

16 em 4a ll. 28 rings. e. part of the molecule originates from the polyketide pathway and part of the compound is derived from the terpene pathway. Many natural products are derived from precursors of two or more biosynthetic origins. 16). 28. 35. 34 em 4a pp ~C02H ll. 32 is also produced as an intermediate in terpene biosynthesis, and this compound can also act as an alkylating agent. 33. 35. 18). 36. 38. 37 0 ll. 38. 19) and we have already met examples of this process in the biosynthesis of unsaturated fatty acids.

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