Total synthesis and determination of the stereochemistry of 2-amino-3-cyclopropylbutanoic acid, a novel plant growth regulator isolated from the mushroom Amanita castanopsidis Hongo.
The unknown stereostructure of 2-amino-3-cyclopropylbutanoic acid 1, a novel plant growth regulator isolated from the mushroom Amanita castanopsidis Hongo, was determined to be (2S,3S)-2 through its racemic and enantioselective syntheses employing the chelate-enolate Claisen rearrangement as a key step.
Morimoto
Yoshiki
Y
Department of Chemistry, Graduate School of Science, Osaka City University, Sumiyoshi-ku, Osaka 558-8585, Japan. morimoto@sci.osaka-cu.ac.jp
Takaishi
Mamoru
M
Kinoshita
Takamasa
T
Sakaguchi
Kazuhiko
K
Shibata
Kozo
K
D000363:Agaricales / Q000737:chemistry*; D000613:Aminobutyrates; D002087:Butyrates / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D010937:Plant Growth Regulators / Q000138:chemical synthesis / Q000737:chemistry* / Q000302:isolation & purification; D016339:Spectrometry, Mass, Fast Atom Bombardment; D013055:Spectrophotometry, Infrared; D013237:Stereoisomerism
C462300:2-amino-3-cyclopropylbutanoic acid; D000613:Aminobutyrates; D002087:Butyrates; D010937:Plant Growth Regulators