Download PDF
Synlett 1994; 1994(8): 594-596
DOI: 10.1055/s-1994-22938
letter
© Georg Thieme Verlag, Rüdigerstr. 14, 70469 Stuttgart, Germany. All rights reserved. This journal, including all individual contributions and illustrations published therein, is legally protected by copyright for the duration of the copyright period. Any use, exploitation or commercialization outside the narrow limits set by copyright legislation, without the publisher's consent, is illegal and liable to criminal prosecution. This applies in particular to photostat reproduction, copying, cyclostyling, mimeographing or duplication of any kind, translating, preparation of microfilms, and electronic data processing and storage.

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
Further Information

Publication History

Publication Date:
18 September 2002 (online)

  PDF Download  Permissions and Reprints All articles of this category

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).