Naturalproductman’s Blog

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Platencin from a Phenol

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.

platencin


OBC paper

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