Naturalproductman’s Blog

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Archive for the ‘retro-Diels-Alder’ Category

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

Posted in Antibiotics, Cascade Reactions, Cycloaddition, Diels-Alder, Hypervalent Iodine, Methodology, Named Reactions, Pericyclic reactions, retro-Diels-Alder | Leave a Comment »

Zearalenone Synthesis

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.

zearalenone

Tetrahedron paper

Posted in Cascade Reactions, Macrocycles, Macrolides, Methodology, Named Reactions, retro-Diels-Alder, Ring forming, Total Synthesis | Leave a Comment »

 
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