title: Synthesis and absolute structure of manzacidin B.
abstract: [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.
authors.affiliation: Graduate School of Science, Osaka City University, Sugimoto, Osaka 558-8585, Japan. shinada@sci.osaka-cu.ac.jp
authors.forename: Tetsuro
authors.initials: T
authors.lastname: Shinada
authors.forename: Eijiro
authors.initials: E
authors.lastname: Ikebe
authors.forename: Kentaro
authors.initials: K
authors.lastname: Oe
authors.forename: Kosuke
authors.initials: K
authors.lastname: Namba
authors.forename: Masanori
authors.initials: M
authors.lastname: Kawasaki
authors.forename: Yasufumi
authors.initials: Y
authors.lastname: Ohfune
mesh_terms: D015394:Molecular Structure; D011743:Pyrimidines / Q000138:chemical synthesis* / Q000737:chemistry; D011758:Pyrroles / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
chemical_list: D011743:Pyrimidines; D011758:Pyrroles; C520151:manzacidin B