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Paper | Special issue | Vol 84, No. 2, 2012, pp.1141-1170
Published online, 8th September, 2011
DOI: 10.3987/COM-11-S(P)95
Convergent Total Syntheses of the Pentacyclic Lamellarins K, T, U and W via the Addition of Azomethine Ylides to Tethered Tolans

Bernard L. Flynn and Martin G. Banwell*

*Research School of Chemistry, Institute of Advanced Studies, The Australian National University, Canberra, ACT 0200, Australia

Abstract

The title compounds, 14 respectively, have been prepared in a concise and fully regiocontrolled manner via the addition of an azomethine ylide to an ester-linked tolan. The resulting annulated dihydropyrrole was oxidized to the corresponding fully aromatic system and the associated isopropyl ethers then selectively cleaved with aluminium trichloride to reveal the free phenolic hydroxyl groups associated with the target compounds.