Stereoselective Access to Tetrahydropyranylacetic Acid-Derivatives - Simple Synthesis of (+)-(S,S)-(Cis-6-Methyltetrahydropyran-2-Yl)Acetic Acid
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Ragoussis, V.
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Πανεπιστήμιο Ιωαννίνων. Σχολή Θετικών Επιστημών. Τμήμα Χημείας
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Ragoussis, V.
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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.
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