Acyl polymalonate pathway

The fatty acid pathway or, as we should call it now, the acyl polymalonate pathway, also gives rise to an inexhaustible variety of aromatic and other compounds belonging to the family of the polyketides. You saw in Chapter 50 how the shikimic acid pathway makes aromatic compounds but the compounds below are from the polyketide route. 

This precise sequence was discovered only through very careful double labelling experiments and after the discovery of specific inhibitors for the enzyme. Since polyketides can be made from the acyl polymalonate pathway with or without reduction and elimination at any step, the number of possible structures is vast. With more reduction, no aromatic ring can be formed macrolide antibiotics such as brefeldin A come from this route. 

Olivetol has the characteristic 1,3-diOH pattern of a polyketide around the benzene ring but it has only 11 carbon atoms so CO2 was probably lost somewhere and the long side chain has certainly been reduced. The acyl-polymalonate pathway (pp. 1425-36) needs to be used. We start from... 

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