They can be synthesized by adding peroxyacid to a cyclic ketone in the Bayer-Villiger reaction or by an intermolecular Fischer reaction.
The bromo-enol type of these compounds are potent inhibitors of calcium-independent phospholipase A2. The quercus one of these compounds is absorbed from whiskey into the wood of barrels, and the Prelog-Djerassi one is a common synthetic test of stereochemical control. Corey's synthesis of prostaglandins has an intermediate consisting of Corey's namesake one of these functional groups with 4-phenyl-benzoate attached. Biological examples of these functional groups include sesquiterpene ones, which include the anti-malarial drug artemisinin, and acylated (*) homoserine ones, which serve as autoinducers in bacterial quorum sensing. Macrocyclic examples of this functional group are found in a class of antibiotics that inhibit the 50S peptidyl-transferase of the bacterial ribosome and which include azithromycin. Gamma and delta ones are the most stable due to ring strain. They can be synthesized by adding peroxyacid to a cyclic ketone in the Bayer-Villiger reaction or by an intermolecular Fischer reaction. For 10 points, name these cyclic esters.
The bromo-enol type of these compounds are potent inhibitors of calcium-independent phospholipase A2.
lactone [prompt on “ester”, do NOT accept or prompt on “orthoester”; accept macrolides]