Total syntheses of (2S)-antafumicins A and B.
To clarify the absolute configurations of antafumicins A and B, which are antifungal substances from Aspergillus niger NH-401, the total synthesis of (2S)-antafumicins was accomplished by starting from (S)-malic acid in 12 steps. Based upon the physicochemical data of the synthetic samples, the absolute configurations of naturally occurring antafumicins A and B were determined as (2R,4S)- and (2R,4R)-4-(3-acetyl-2,6-dihydroxyphenyl)-2-methoxy-4-butanolide, respectively.
Fujimoto
Y
Y
Analytical Chemistry Research Laboratory, Tanabe Seiyaku Co. Ltd., Osaka, Japan.
Ukita
T
T
Miyagawa
H
H
Tsurushima
T
T
Irie
H
H
Nishimura
K
K
Ueno
T
T
D015107:4-Butyrolactone / Q000031:analogs & derivatives / Q000138:chemical synthesis; D000935:Antifungal Agents / Q000138:chemical synthesis*; D001234:Aspergillus niger / Q000378:metabolism; D008293:Malates / Q000737:chemistry; D015394:Molecular Structure; D013237:Stereoisomerism
D000935:Antifungal Agents; D008293:Malates; C090215:antafumicin A; C030298:malic acid; D015107:4-Butyrolactone