Author(s): Habel A, Boland W
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Abstract An efficient and highly flexible synthesis for chiral gamma- and delta-lactones with high enantiomeric purity is described (>99\% ee and 57-87\% overall yield). The protocol involves alkylation of chiral 1,2-oxiranes with terminally unsaturated Grignard reagents. Subsequent oxidative degradation (OsO(4)-Oxone) of the terminal double bond from chiral alk-1-en-5-ols and alk-1-en-6-ols affords 4- or 5-hydroxy acids and gamma- and delta-lactones after acidic workup. The flexibility and efficiency of the protocol is illustrated by the synthesis of several alkanolides and alkenolides, hydroxy fatty acids and dihydroisocoumarins.
This article was published in Org Biomol Chem
and referenced in Journal of Applied Pharmacy