A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation

A concise synthetic approach to brazilin via Pd-catalyzed allylic arylation

A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling...

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Veröffentlicht in:Organic & biomolecular chemistry 2015-04, Vol.13 (14), p.4331-4335
Hauptverfasser: Jung, Youngeun, Kim, Ikyon
Format: Artikel
Sprache:eng
Schlagworte:
Acetates - chemistry
Allyl Compounds - chemistry
Benzopyrans - chemical synthesis
Benzopyrans - chemistry
Catalysis
Chemistry Techniques, Synthetic
Cyclization
Palladium - chemistry
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Zusammenfassung:A short synthetic route to the trimethyl ether of brazilin was developed in 6 steps from 7-methoxychromene with 78% overall yield. Regioselective installation of a formyl group onto 7-methoxychromene followed by reduction and acetylation afforded allylic acetate. Palladium-catalyzed allylic coupling of allylic acetate with arylboronic acid provided direct access to 3-benzylchromene which was converted to the target molecule upon ensuing dihydroxylation and acid-catalyzed cyclization in a highly concise manner.
ISSN:1477-0520
1477-0539
DOI:10.1039/c5ob00216h