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Synlett 1994; 1994(8): 594-596
DOI: 10.1055/s-1994-22938
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3-Methoxy-1-phenylthio-1-propene as d1 / d3 Synthon: Application for an Asymmetric Synthesis of (S)-(+)-Parasorbic Acid

Ralf Tiedemann* , Frank Narjes, Ernst Schaumann
  • *Institut für Organische Chemie, Technische Universität Clausthal, Leibnizstrasse 6, D-38678 Clausthal-Zellerfeld, Germany
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Publication Date:
18 September 2002 (online)

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Regioselective ring-opening of oxiranes with the sulfurstabilized anion 1 of 3-methoxy-1-phenylthio-1-propene and acidcatalyzed cyclization of the resulting bishomoallyl alcohols 2a-f leading to the tetrahydropyrans 3a-f are key-steps in the synthesis of α,β-unsaturated δ-lactones. An enantioselective synthesis of (S)-(+)-parasorbic acid (14) has been developed starting from (S)-(-)-epoxypropane (9).

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