Stereocontrolled Synthesis of the Daphenylline Pentacyclic ACDEF Ring System.
Sergi JansanaFaïza DiabaJosep BonjochPublished in: Organic letters (2019)
An azapentacyclic compound with the daphenylline ACDEF ring framework was synthesized from a benzo[e]indole intermediate efficiently obtained by a 5-endo-trig radical cyclization of a bicyclic trichloroenamide. Stereocontrolled processes were used to generate the three stereogenic methine carbons in the pyrrolidine C ring including the all-carbon quaternary stereocenter at C5. Ring closure to build both seven- and five-membered rings was achieved by Friedel-Crafts reactions.
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