Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity

Takahiro YOSHIDA; Satoshi YAMAUCHI; Ryosuke TAGO; Masafumi MARUYAMA; Koichi AKIYAMA; Takuya SUGAHARA; Taro KISHIDA; Yojiro KOBA

doi:10.1271/bbb.80262

This article has now been updated. Please use the final version.

Syntheses of All Stereoisomers of Goniodiol from Yeast-Reduction Products and Their Antimicrobiological Activity

Takahiro YOSHIDA, Satoshi YAMAUCHI, Ryosuke TAGO, Masafumi MARUYAMA, Koichi AKIYAMA, Takuya SUGAHARA, Taro KISHIDA, Yojiro KOBA

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Keywords: goniodiol, yeast-reduction product, antimicrobiological activity

JOURNAL FREE ACCESS Advance online publication

Article ID: 80262

DOI https://doi.org/10.1271/bbb.80262

The final version of this article is now available: Vol. 72 (2008) , No. 9 p.2342

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Abstract

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.

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