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Stereoselective synthesis of thienyl and furyl analogues of ephedrine

✍ Scribed by Franz Effenberger; Joachim Eichhorn

Publisher: Elsevier Science
Year: 1997
Tongue: English
Weight: 503 KB
Volume: 8
Category: Article
ISSN: 0957-4166
DOI: 10.1016/s0957-4166(96)00528-9

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✦ Synopsis

The stereoselective syntheses of thienyl and furyl analogues of ephedrine starting from (R)-and (S)-cyanohydrins, respectively, are described. Addition of methyl Grignard to the O-trimethylsilyl protected optically active cyanohydrins (R)-and (S)-3 and hydrogenation of the resulting imino intermediates gives the erythro-2-amino alcohols 4 with high diastereoselectivity. Their reductive methylation leads to the enantiomerically pure thiophene analogues (1S,2S)-and (1R,2R)-6a, (1R,2S)-and (1S,2R)-6b as well as to the furan analogues (1S,2S)-6c and (IR,2S)-6d of ephedrine. The biological activity of the new compounds is under investigation.

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