Efficient and flexible synthesis of chiral γ- and δ-lactones

Andreas Habel; Wilhelm Boland

doi:10.1039/B801514G

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Organic & Biomolecular Chemistry

Issue 9, 2008

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Efficient and flexible synthesis of chiral γ- and δ-lactones

Andreas Habel and Wilhelm Boland

Org. Biomol. Chem., 2008, 6, 1601-1604

DOI: 10.1039/B801514G
Received 28 Jan 2008, Accepted 01 Feb 2008
First published on the web 10 Mar 2008

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Abstract
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An efficient and highly flexible synthesis for chiral γ- and δ-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 γ- and δ-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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General experimental, synthesis of substrates and spectra for compounds
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Organic & Biomolecular Chemistry

Efficient and flexible synthesis of chiral γ- and δ-lactones

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