A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones
- 1 January 1991
- journal article
- Published by Institute of Organic Chemistry & Biochemistry in Collection of Czechoslovak Chemical Communications
- Vol. 56 (5) , 1042-1051
- https://doi.org/10.1135/cccc19911042
Abstract
The tert-butyl propiolate ion serves as a convenient and efficient nucleophile in boron trifluoride-catalyzed openings of homochiral, mono-substituted epoxides. The resulting tert-butyl 5-hydroxy-2-alkynoates are converted into the title compounds upon semihydrogenation followed by acid hydrolysis. Specific examples include the synthesis of parasorbic acid and massoilactone, two naturally derived lactones of the present type. The scope of the synthetic protocol is discussed.Keywords
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