Posted by naturalproductman on August 5, 2010
Vishwakarma Singh and co-workers from IIT Bombay have published in Organic and Biomolecular Chemistry on an oxidation of a phenol that yields a Diels-Alder substrate that dimerizes on itself and when the dimer is heated reforms the dienone substrate that undergoes an intramolecular Diels-Alder reaction. So the sequence goes like so: intermolecular Diels-Alder to retro-Diels-Alder to intramolecular Diels-Alder – all to yield platencin’s polycyclic structure.
Posted in Antibiotics, Cascade Reactions, Cycloaddition, Diels-Alder, Hypervalent Iodine, Methodology, Named Reactions, Pericyclic reactions, retro-Diels-Alder | Leave a Comment »
Posted by naturalproductman on July 20, 2010
Anthony Barrett and co-workers at Imperial College have published in Tetrahedron on the synthesis of zearalenone a macrocycle with an aromatic group embedded in the compound. The macrocyclic portion was synthesized by forming a ketene and trapping it with an alcohol in situ and the aromatic group was synthesized from a triketone.
Posted in Cascade Reactions, Macrocycles, Macrolides, Methodology, Named Reactions, retro-Diels-Alder, Ring forming, Total Synthesis | Leave a Comment »