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Synthesis of (3 R ,4 R )‐3‐Amino‐4‐hydroxyhexahydroazepine, the Chiral Constituent of the Antibiotic Ophiocordin
Author(s) -
Müller Alexander,
Takyar Dinesh K.,
Witt Sandra,
König Wilfried A.
Publication year - 1993
Publication title -
liebigs annalen der chemie
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.825
H-Index - 155
eISSN - 1099-0690
pISSN - 0170-2041
DOI - 10.1002/jlac.1993199301106
Subject(s) - chemistry , moiety , enantioselective synthesis , absolute configuration , stereochemistry , antifungal , optically active , serine , antibiotics , amino acid , chiral column chromatography , enantiomer , organic chemistry , catalysis , biochemistry , microbiology and biotechnology , biology , enzyme
(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.