(opens in new window) Buy Article (opens in new window) Permissions and Reprints (opens in new window) All articles of this category (opens in new window) 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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Tiedemann et al. (1994) studied this question.