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Pyran derivativesR 0340 A Diastereoselective Route to 2,6-syn-Disubstituted Tetrahydropyrans: Synthesis

of the Civet Compound (+)-2-((2S,6S)-6-Methyltetrahydro-2H-pyran-2-yl) Acetic Acid. — A diastereoselective synthesis of 2,6-syn-disubstituted tetrahydrofurans is based on the ability of furanyl-ether chiral centers to epimerize under acidic conditions. The novel methodology is applied to the synthesis of natural product (VIII). — (O'BRIEN*, M.; CAHILL, S.; EVANS, L. A.; Chem. Commun. (Cambridge) 2008, 43, 5559-5561; Whiffen Lab., Dep. Chem., Univ. Cambridge, Cambridge CB2 1EW, UK; Eng.) — M. Paetzel

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ChemInform 2009, 40, issue 13 © 2009 Wiley-VCH Verlag GmbH & Co. KGaA, Weinheim