Four unprecedented chlorinated monoterpenyl quinolones have been isolated using a molecular networking based prioritisation strategy. The bio-inspired total synthesis of chloroaustralasine A involving a chloroperoxydase-mediated hydroxychlorination is described.

We herein described an intramolecular imino Diels−Alder reaction promoted with BF3·OEt2/DDQ affording substituted quinolines. Using this procedure, we prepared the chiral quinoline moiety of the uncialamycin, a new enediyne natural product.