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John E. Lynch, Dr. Shannon D. Zanatta, Prof. Dr. Jonathan M. White and Prof. Dr. Mark A. Rizzacasa Stereoselective Total Synthesis of (−)-Spirofungin A by Utilising Hydrogen-Bond Controlled Spiroketalisation Chemistry - A European Journal 17

Version of Record online: 10 DEC 2010 | DOI: 10.1002/chem.201002501

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Spiro key: The stereoselective total synthesis of the spiroketal-containing Streptomyces metabolite (−)-spirofungin A (1) is described. A key step involved a spiroketalisation controlled by an intramolecular hydrogen bond, which favoured the desired spiroketal 2 (13:1 ratio). Other key steps include an efficient cross-metathesis to form the spiroketal precursor and a Stille cross-coupling reaction. A final Wittig extension followed by deprotection gave 1.

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