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Synthesis 1993; 1993(1): 84-86
DOI: 10.1055/s-1993-25803
short paper
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Stereoselective Access to Tetrahydropyranylacetic Acid Derivatives. Simple Synthesis of (+)-(S,S)-(cis-6-Methyltetrahydropyran-2- yl)acetic Acid

Valentine Ragoussis* , Vassiliki Theodorou
  • *Laboratory of Organic Chemistry, University of Athens, Panepistimiopolis, Zografou, G-157-71 Athens, Greece
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Publication Date:
17 September 2002 (online)

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The reaction of the lactols 1a-1d, with malonic acid in hot dimethyl sulfoxide, in the presence of piperidinium acetate as catalyst, gives the corresponding (tetrahydrofuran-2-yl)acetic acids 2a,c and (tetrahydropyran-2-yl)acetic acids 2b,d in high yield (65-75%). While the synthesis of the (6-methyltetrahydropyran-2-yl)acetic acid (2d) 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.