Stereoselective Access to Tetrahydropyranylacetic Acid-Derivatives - Simple Synthesis of (+)-(S,S)-(Cis-6-Methyltetrahydropyran-2-Yl)Acetic Acid

 
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1993 (EN)
Stereoselective Access to Tetrahydropyranylacetic Acid-Derivatives - Simple Synthesis of (+)-(S,S)-(Cis-6-Methyltetrahydropyran-2-Yl)Acetic Acid (EN)

Ragoussis, V. (EN)

Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας (EL)
Ragoussis, V. (EN)

The reaction of the lactols 1 a-1 d, with malonic acid in hot dimethyl sulfoxide, in the presence of piperidinium acetate as catalyst, gives the corresponding (tetrahydrofuran-2-yl)acetic acids 2 a, c and (tetrahydropyran-2-yl)acetic acids 2 b, d in high yield (65-75 %). While the synthesis of the (6-methyltetrahydropyran-2-yl)acetic acid (2 d) is highly stereoselective (cis/trans ratio 20:1), no stereoselection was observed with the (5-methyltetrahydrofuran-2-yl)acetic acid (2c) (cis/trans ratio 1:1). This reaction was applied for the synthesis of natural (+)-(S,S)-(cis-6-methyltetrahydropyran-2-yl)acetic acid (7), minor constituent of the glandular secretion of the civet cat. (EN)

trans-2,5-disubstituted tetrahydrofurans (EN)

Πανεπιστήμιο Ιωαννίνων (EL)
University of Ioannina (EN)

Synthesis-Stuttgart (EN)

English

1993

<Go to ISI>://A1993KK38300026

Thieme Publishing (EN)



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