Systematic strategy for the synthesis of cyanobacterin and its stereoisomers. 2. Asymmetric total synthesis of the 2- and 3-epimers of dechloro-cyanobacterin.
Stereocontrolled total syntheses of the (2S,3R)- and (2R,3S)-isomers of the non-chlorinated analog of cyanobacterin, a potent photosynthesis inhibitor, were achieved. Since both the (2R,3R)- and (2S,3S)-isomers of this compound had been previously synthesized from the same starting material, a systematic strategy for the synthesis of all stereoisomers could be established.
Haga
Yasushi
Y
The United Graduate School of Agricultural Science, Ehime University, Tarumi, Matsuyama, Japan. haga@agr.ehime-u.ac.jp
Okazaki
Momotoshi
M
Shuto
Yoshihiro
Y
D015107:4-Butyrolactone / Q000031:analogs & derivatives* / Q000138:chemical synthesis*; D000480:Alkynes / Q000737:chemistry; D009682:Magnetic Resonance Spectroscopy; D015394:Molecular Structure; D013237:Stereoisomerism
D000480:Alkynes; C487923:dechloro-cyanobacterin; C033701:cyanobacterin; D015107:4-Butyrolactone