Web Release Date: August 2,
Synthesis of (±)-5-epi-Citreoviral and (±)-Citreoviral and the Kinetic Resolution of an Allylic Silane by a [3 + 2] Annulation
Department of Chemistry, University of California, Irvine, California 92697-2025
Received June 11, 2002
| Abstract: |
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-keto ester provided the highly substituted tetrahydrofuran 2 as a single diastereomer
in high yield. The synthesis of (±)-5-epi-citreoviral and (±)-citreoviral has been accomplished with this annulation reaction as the key step.
Using the pantolactone-derived -keto ester, the allylsilane 1 has been resolved with high enantiomeric purity.
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