3-METHOXY-1-PHENYLTHIO-1-PROPENE AS D1/D3 SYNTHON - APPLICATION FOR AN ASYMMETRIC-SYNTHESIS OF (S)-(+)-PARASORBIC ACID

Regioselective ring-opening of oxiranes with the sulfur-stabilized anion 1 of 3-methoxy-1-phenylthio-1-propene and acid-catalyzed cyclization of the resulting bishomoallyl alcohols 2a-f leading to the tetrahydropyrans 3a-f are key-steps in the synthesis of alpha,beta-unsaturated delta-lactones. An e...

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Bibliographic Details
Published inSynlett no. 8; pp. 594 - 596
Main Authors TIEDEMANN, R, NARJES, F, SCHAUMANN, E
Format Journal Article
LanguageEnglish
Published STUTTGART Thieme Medical Publishers 01.08.1994
Subjects
Chemistry
Chemistry, Organic
Physical Sciences
Science & Technology
OXIRANES
ALLYL ANION
NATURAL-PRODUCTS
ASYMMETRIC SYNTHESIS
DELTA-LACTONES
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Summary:Regioselective ring-opening of oxiranes with the sulfur-stabilized anion 1 of 3-methoxy-1-phenylthio-1-propene and acid-catalyzed cyclization of the resulting bishomoallyl alcohols 2a-f leading to the tetrahydropyrans 3a-f are key-steps in the synthesis of alpha,beta-unsaturated delta-lactones. An enantioselective synthesis of (S)-(+)-parasorbic acid (14) has been developed starting from (S)-(-)-epoxypropane (9).
ISSN:0936-5214
DOI:10.1055/s-1994-22938