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Paper | Special issue | Vol 70, No. 1, 2006, pp.321-334
Published online, 10th October, 2006
DOI: 10.3987/COM-06-S(W)28
A Chiral Pool Approach toward the Synthesis of Thalidomide Metabolites

Frederick A. Luzzio,* Damien Y. Duveau, and William D. Figg

*Department of Chemistry, University of Louisville, 2320 South Brook Streeet, Louisville, KY 40292, U.S.A.

Abstract

A synthetic strategy toward the glutarimide-derived metabolite of thalidomide, 5’-hydroxythalidomide (5’-OH THD, 2) was developed which utilizes aspartic acid as a “chiral pool”-type starting material. The synthesis incorporates a Henry reaction as the key carbon-carbon bond-forming step followed by a tandem reduction-cyclization of the intermediate nitroalcohol in forming the heterocyclic core of 5’-OH THD