Stereocontrolled Synthesis of the Daphenylline Pentacyclic ACDEF Ring System.

Authors:
Dr. Faiza Diaba, PhD
Dr. Faiza Diaba, PhD
Barcelona University
Professor
Barcelona, Not US or Canada | Spain

Org Lett 2019 Jul 2;21(14):5757-5761. Epub 2019 Jul 2.

Laboratori de Química Orgànica, Facultat de Farmàcia, IBUB , Universitat de Barcelona , Av. Joan XXIII s/n , Barcelona 08028 , Spain.

An azapentacyclic compound with the daphenylline ACDEF ring framework was synthesized from a benzo[]indole intermediate efficiently obtained by a 5-- 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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http://dx.doi.org/10.1021/acs.orglett.9b02211DOI Listing
July 2019
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