Platencin from a Phenol

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.

OBC paper

Zearalenone Synthesis

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.

Tetrahedron paper