Stereoselective synthesis of (-)-cytoxazone and (+)-epi-cytoxazone
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Optically pure (-)-cytoxazone was synthesized, starting from methyl p-methoxycinnamate, in six steps and in 31%, overall yield. The required anti-aminoalcohol configuration was established by combining Sharpless asymmetric aminohydroxylation with the configurational inversion of the intermediate amidoalcohol via ail oxazoline. The synthesis of (+)-epi-cytoxazone is also described. (C) 2003 Elsevier Ltd. All rights reserved.
Keywords:cytoxazone / asymmetric synthesis / natural products / immunosuppressive compounds / amino alcohols
Source:Tetrahedron Letters, 2004, 45, 5, 955-957
- Pergamon-Elsevier Science Ltd, Oxford