Yoshida Takahiro, Yamauchi Satoshi, Tago Ryosuke, Maruyama Masafumi, Akiyama Koichi, Sugahara Takuya, Kishida Taro, Koba Yojiro
Faculty of Agriculture, Ehime University, Tarumi, Matsuyama, Ehime, Japan.
Biosci Biotechnol Biochem. 2008 Sep;72(9):2342-52. doi: 10.1271/bbb.80262. Epub 2008 Sep 7.
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.