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Paper
Org. Biomol. Chem., 2008, 6, 1601 - 1604, DOI: 10.1039/b801514g
Efficient and flexible synthesis of chiral
- and 
-lactonesAndreas Habel and Wilhelm Boland
An efficient and highly flexible synthesis for chiral
- and 
-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 (OsO4–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 - and -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.
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