Syntheses of all stereoisomers of goniodiol from yeast-reduction products and their antimicrobiological activity.
All stereoisomers of goniodiol were synthesized from yeast-reduction products. The C-6 chiral centers were converted from the chiral centers of the yeast-reduction products. Stereoselective conversion of the alkene, which had been prepared from the yeast-reduction product, to glycol constructed the C-7 and C-8 stereochemistry. (+)-Goniodiol and 7-epi-(+)-goniodiol showed the highest antibacterial activity (MIC, 3.1 mM) against Yersinia intermedia.
Yoshida
Takahiro
T
Faculty of Agriculture, Ehime University, Tarumi, Matsuyama, Ehime, Japan.
Yamauchi
Satoshi
S
Tago
Ryosuke
R
Maruyama
Masafumi
M
Akiyama
Koichi
K
Sugahara
Takuya
T
Kishida
Taro
T
Koba
Yojiro
Y
D000438:Alcohols / Q000737:chemistry; D000475:Alkenes / Q000737:chemistry; D000900:Anti-Bacterial Agents / Q000138:chemical synthesis* / Q000737:chemistry / Q000494:pharmacology; D005663:Furans / Q000737:chemistry; D008826:Microbial Sensitivity Tests; D008968:Molecular Conformation; D015394:Molecular Structure; D009904:Optical Rotation; D011753:Pyrones / Q000737:chemistry*; D013237:Stereoisomerism; D013329:Structure-Activity Relationship; D015003:Yeasts / Q000737:chemistry*; D015007:Yersinia / Q000187:drug effects
D000438:Alcohols; D000475:Alkenes; D000900:Anti-Bacterial Agents; D005663:Furans; D011753:Pyrones; C446739:goniodiol