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

T Høyer, A Kjær, J Lykkesfeldt

Index: Hoeyer, Thomas; Kjaer, Anders; Lykkesfeldt, Jens Collection of Czechoslovak Chemical Communications, 1991 , vol. 56, # 5 p. 1042 - 1051

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Citation Number: 18

Abstract

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 ...

 Related Synthetic Route
(S)-Heptane-1,2-diol Structure

61229-00-3

(S)-Heptane-1,2-diol

~%

(S)-(-)-1,2-Epoxyoctane Structure

61229-03-6

(S)-(-)-1,2-Epo...

rac-2,2-dimethyl-4-(3'-hydroxypropyl)-1,3-dioxolan toluene-p-sulphonate Structure

135027-61-1

rac-2,2-dimethy...

~%

(S)-(-)-1,2-Epoxyoctane Structure

61229-03-6

(S)-(-)-1,2-Epo...

(R)-(+)-1,2-HEPTANEDIOL Structure

78843-64-8

(R)-(+)-1,2-HEP...

~%

(R)-(+)-1,2-Epoxyheptane Structure

110549-07-0

(R)-(+)-1,2-Epo...

2,2-dimethyl-4-pentyl-[1,3]dioxolane Structure

60045-13-8

2,2-dimethyl-4-...

~%

(R)-(+)-1,2-Epoxyheptane Structure

110549-07-0

(R)-(+)-1,2-Epo...

rac-2,2-dimethyl-4-(3'-hydroxypropyl)-1,3-dioxolan toluene-p-sulphonate Structure

135358-19-9

rac-2,2-dimethy...

~%

(R)-(+)-1,2-Epoxyheptane Structure

110549-07-0

(R)-(+)-1,2-Epo...

(R)-tert-butyl-5-hydroxy-2-decynoate Structure

135358-20-2

(R)-tert-butyl-...

~%

(R)-2-decen-5-olide Structure

51154-96-2

(R)-2-decen-5-olide

(R)-(+)-1,2-HEPTANEDIOL Structure

78843-64-8

(R)-(+)-1,2-HEP...

~%

(R)-2-decen-5-olide Structure

51154-96-2

(R)-2-decen-5-olide

2,2-dimethyl-4-pentyl-[1,3]dioxolane Structure

60045-13-8

2,2-dimethyl-4-...

~%

(R)-2-decen-5-olide Structure

51154-96-2

(R)-2-decen-5-olide

rac-2,2-dimethyl-4-(3'-hydroxypropyl)-1,3-dioxolan toluene-p-sulphonate Structure

135358-19-9

rac-2,2-dimethy...

~%

(R)-2-decen-5-olide Structure

51154-96-2

(R)-2-decen-5-olide

tert-Butyldimethylsilyl chloride Structure

18162-48-6

tert-Butyldimet...

Isopropanol Structure

67-63-0

Isopropanol

~77%

t-Butyl Dimethyl Isopropoxylsilane Structure

17348-66-2

t-Butyl Dimethy...


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