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Published on: April 4, 2014
Convergent Synthesis of (R)-Silodosin via Decarboxylative Cross-Coupling
Tie-Gen Chen1, Lucas Mele2, Olivier Jentzer2
1Department of Chemistry, Scripps Research, 10550 North Torrey Pines Road, La Jolla, California 92037, United States.
Abstract:
A new approach to Silodosin capitalizing on a radical retrosynthetic strategy to dissect the molecule into two halves is reported. Using a reductive decarboxylative cross-coupling, a simple indoline can be coupled to a chiral pool-derived fragment to arrive at the target in only seven steps (LLS). This route avoids the use of resolution strategies or asymmetric hydrogenation that requires a subsequent Curtius rearrangement to install a key amino functionality.
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