Synthesis and absolute structure of manzacidin B.
[reaction: see text] Four possible stereoisomers of manzacidin B were synthesized using stereochemically defined synthetic routes via the azide 7 and oxazoline 11 starting with the (R)-alpha-methyl Garner aldehyde 5. Comparisons of the spectroscopic data of the synthetic isomers 4a-d with those of the natural manzacidin B revised the proposed structure 3 to (4S,5S,6R)-4d.
Shinada
Tetsuro
T
Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Japan. shinada@sci.osaka-cu.ac.jp
Ikebe
Eijiro
E
Oe
Kentaro
K
Namba
Kosuke
K
Kawasaki
Masanori
M
Ohfune
Yasufumi
Y
D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
D011743:Pyrimidines; D011758:Pyrroles; C520151:manzacidin B