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Synthesis of (3R,4R)-3-Amino-4-hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin

✍ Scribed by Müller, Alexander ;Takyar, Dinesh K. ;Witt, Sandra ;König, Wilfried A.

Book ID
102900946
Publisher
John Wiley and Sons
Year
1993
Tongue
English
Weight
537 KB
Volume
1993
Category
Article
ISSN
0947-3440

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✦ Synopsis

Abstract

(3__R__,4__R__)‐3‐Amino‐4‐hydroxyhexahydroazepine (2), the optically active constituent of the antifungal antibiotic ophiocordin (1), was prepared in a multistep synthesis starting from D‐serine. The absolute configuration was unambigously assigned by a comparison of the synthesized stereoisomer 2 with its racemate and the chiral moiety of the antibiotic ophiocordin by enantioselective gas chromatography.

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