3-Methoxy-1-phenylthio-1-propene as d1/ d3Synthon: Application for an Asymmetric Synthesis of (S)-(+)-Parasorbic Acid
- 1 January 1994
- journal article
- letter
- Published by Georg Thieme Verlag KG in Synlett
- Vol. 1994 (08) , 594-596
- https://doi.org/10.1055/s-1994-22938
Abstract
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).Keywords
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