Synthesis of (3S, 4S)-3, 4-Dihydroxyprolines from L-Tartaric Acid

Yasushi ARAKAWA; Shigeyuki YOSHIFUJI

doi:10.1248/cpb.39.2219

Chemical and Pharmaceutical Bulletin

Online ISSN : 1347-5223
Print ISSN : 0009-2363

Synthesis of (3S, 4S)-3, 4-Dihydroxyprolines from L-Tartaric Acid

Yasushi ARAKAWA, Shigeyuki YOSHIFUJI

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Keywords: (2S, 3S, 4S)-3, 4-dihydroxyproline, (2R, 3S, 4S)-3, 4-dihydroxyproline, L-tartaric acid, (3S, 4S)-3, 4-dihydroxypyrrolidine, NOE difference spectrum, N-chlorosuccinimide, 1, 8-diazabicyclo[5.4.0]-7-undecene, cyclic Schiff base, cyanotrimethysilane, zinc iodide, diastereoselectivity

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Volume 39 (1991) Issue 9 Pages 2219-2224

DOI https://doi.org/10.1248/cpb.39.2219

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Abstract

Natural (2S, 3S, 4S)-3, 4-dihydroxyproline (1) and the new (2R, 3S, 4S)-isomer (7) have been synthesized from L-tartaric acid via cyanosilylation of the cyclic Schiff base.

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