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Syntheses of (S)- and (R)-dihydromethysticin from two yeast-reduction products, which can be prepared from one racemic compound
Phytochemistry Letters ( IF 1.3 ) Pub Date : 2024-02-09 , DOI: 10.1016/j.phytol.2024.02.001
Kento Tamada , Hisashi Nishiwaki , Satoshi Yamauchi

Biologically active ()-Dihydromethysticin (()-) with high enantiomeric purity (>99%ee) was synthesized from the optically active yeast-reduction product, (1 ,2 )-methyl 2-hydroxycyclohexyl acetate (), through the introduction of the 3,4-methylenedioxybenzyl group, Beayer-Villiger oxidation, and conversion to its enolate. Moreover, ()-Dihydromethysticin (()-) with high enantiomeric purity (>99%ee) was synthesized from the optically active yeast-reduction product, (1 ,5 )− 2-oxabicyclo[3.3.0]octan-3-one (), employing the same synthetic method used for ()-. The antifungal activity of both these enantiomers against and was found to be weak.

中文翻译:

从两种酵母还原产物合成 (S)- 和 (R)-二氢迷幻素,可以由一种外消旋化合物制备

以光学活性酵母还原产物乙酸(1,2)-甲基2-羟基环己酯()为原料,通过引入3,4-亚甲二氧基苄基、Beayer-Villiger 氧化以及转化为其烯醇化物。此外,从光学活性酵母还原产物(1 ,5 )− 2-氧杂双环[3.3.0]辛烷-3-合成了具有高对映体纯度(>99%ee)的()-二氢迷幻素(()-)。一个(),采用与()-相同的合成方法。发现这两种对映体的抗真菌活性都很弱。
更新日期:2024-02-09
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