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Synthesis of a D-ring Isomer of Galanthamine via a Radical-Based Smiles Rearrangement Reaction

Ping Lan, Colin J Jackson, Martin G Banwell, Anthony C Willis

J Org Chem. 2014 Jul 18;79(14):6759-64.

PMID: 24978095

Abstract:

The 1,9-ethanoiminomethano-bridged tetrahydrodibenzo[b,d]-furan 2, a non-natural isomer of the alkaloid (-)-galanthamine (1) varying in the manner in which the D-ring is annulated to the ABC-core, has been prepared in racemic form. The synthetic sequence starts with the cyclopropane 3 and involves intramolecular Heck alkenylation and radical-based Smiles rearrangement reactions as key steps. Unlike natural product 1, but as predicted by docking studies, compound 2 is not a potent inhibitor of acetylcholine esterase.

Chemicals Related in the Paper:

Catalog Number Product Name Structure CAS Number Price
AP193146859 Galantamine hydrobromide racemic Galantamine hydrobromide racemic 193146-85-9 Price
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