The diagram below shows the biogenesis of the oxazole ring from serine and malonate.
2.
All of the carbons in oxazolidines are reduced ( compare to oxazole and oxazoline ).
3.
*In one reported oxazole synthesis the reactants are a nitro-substituted benzoyl chloride and an isonitrile:
4.
Rhizoxin is a 16-membered lactone ring connected to an oxazole ring by a long unsaturated chain.
5.
The first part of this reaction is the cyclization of an 2-acylamidoketone that contains all three oxazole substituents.
6.
The oxazole is formed from the Ugi intermediate, which is ideal to undergo Robinson-Gabriel cyclodehydration with sulfuric acid.
7.
Labeling studies have determined that the amide oxygen is the most Lewis basic and therefore is the one included in the oxazole.
8.
Another round of malonate extension occurs, followed by the malonate's reaction with an adjacent serine extender to form an oxazole ring.
9.
This process converts cysteine and serine / threonine residues into thiazole and ( methyl ) oxazole heterocycles ( as seen to the right ).
10.
Additionally, a coupled Ugi and Robinson Gabriel synthesis has been reported, beginning with the Ugi reagents and ending with an oxazole core within the molecule.
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