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Synlett 1995; 1995(8): 869-870
DOI: 10.1055/s-1995-5087
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Diastereo- and Enantioselective Synthesis of (-)-Oudemansin A via [2,3]-Wittig Rearrangement of Crotyloxyacetaldehyde-SAEP-Hydrazone

Dieter Enders* , Michael Bartsch, Dirk Backhaus
  • *Institut für Organische Chemie, Rheinisch-Westfälische Technische Hochschule, Professor-Pirlet-Straße 1, D-52074 Aachen, Germany
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Publication History

Publication Date:
31 December 2000 (online)

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The total synthesis of (-)-oudemansin A (1) was accomplished in a ten-step sequence with good overall yield (20 %) and excellent diastereo- and enantiomeric excesses (de, ee ≥ 98 %). Key step of the synthesis is the asymmetric [2,3]-Wittig rearrangement of crotyloxyacetaldehyde-SAEP-hydrazone [(S)-6].

oudemansin A - [2,3]-Wittig rearrangement - magnesium monoperoxyphthalate - chiral hydrazone - asymmetric synthesis

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