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Total Synthesis and Determination of the Absolute Configuration of (−)-Dolabriferol


  • We thank the Swiss National Science Foundation (Bern) and the Roche Research Foundation for financial support, Dr. M. L. Ciavatta for copies of the 1H and 13C NMR spectra of natural (−)-1, and Dr. R. Scopellitti and Dr. K. Schenk for X-ray diffraction studies.


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A reaction cascade combining sulfur dioxide with a 1-oxy-1,3-diene and (E)-silyl enol ether formed the basis of a short total synthesis of (−)-dolabriferol (see scheme; TMS=trimethylsilyl). The absolute configuration of this natural product, which was first extracted from a gastropod mollusc in 1996, was established unequivocally.