Gracil(e): The total synthesis of gracilamine features a potentially biomimetic intramolecular [3+2] cycloaddition to assemble its two fused five‐membered rings and a debenzylation/ring‐opening reaction to obtain the aldehyde intermediate (see scheme). The success of this synthesis provides a circumstantial evidence that supports the biosynthesis pathway of gracilamine proposed previously.
Gra„z“il: Die Totalsynthese von Gracilamin umfasst eine intramolekulare [3+2]‐Cycloaddition zum Aufbau der beiden kondensierten fünfgliedrigen Ringe und eine Debenzylierungs‐/Ringöffnungs‐Reaktion, die zum Aldehyd‐Intermediat führt (siehe Schema). Der Erfolg der Synthese ist ein Indiz für die Richtigkeit des vorgeschlagenen Biosynthesewegs.
Herein,
we report a synthetic route for an EGFR inhibitor, 2-(5-fluoro-2-hydroxyphenyl)-2-(1-oxoisoindolin-2-yl)
acetic acid (EAI045), using a three-step approach. This short and
efficient route is the first report of a scalable process for EAI045,
which employs a convergent three-component coupling strategy as the
key step, producing EAI045 in good yield on kilogram scale.
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