A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones

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Title:A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones
Creators:
Høyer, Thomas
Kjær, Anders
Lykkesfeldt, Jens
Journal or Publication Title:
Collection of Czechoslovak Chemical Communications, 56, 5, pp. 1042-1051

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.

Title:A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones
Creators:
Høyer, Thomas
Kjær, Anders
Lykkesfeldt, Jens
Divisions:Life and Chemical Sciences > Institute of Organic Chemistry and Biochemistry > Collection of Czechoslovak Chemical Communications
Journal or Publication Title:Collection of Czechoslovak Chemical Communications
Volume:56
Number:5
Page Range:pp. 1042-1051
ISSN:0010-0765
E-ISSN:1212-6950
Publisher:Institute of Organic Chemistry and Biochemistry
Related URLs:
URLURL Type
http://dx.doi.org/10.1135/cccc19911042UNSPECIFIED
ID Code:5022
Item Type:Article
Deposited On:22 Feb 2010 11:28
Last Modified:22 Feb 2010 10:29

Citation

Høyer, Thomas; Kjær, Anders; Lykkesfeldt, Jens (1991) A convenient synthesis of homochiral δ-alkylated α,β-unsaturated δ-lactones. Collection of Czechoslovak Chemical Communications, 56 (5). pp. 1042-1051. ISSN 0010-0765

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