Enantioselectivity in the Biotransformation of Mono- and Bicyclic Monoterpenoids with the Cultured Cells of<i>Nicotiana tabacum</i>
作者:Hiroki Hamada
DOI:10.1246/bcsj.61.869
日期:1988.3
The biotransformation of the enantiomeric pairs of p-menthane and bicyclo[2.2.1] and [3.1.1]heptane derivatives with the culturedcells of Nicotianatabacum was investigated. It was found that (i) the culturedcells discriminate the enantiomers of p-menthan-2-ol and bicyclo[2.2.1]heptan-2-ol and bicyclo[3.1.1]heptan-3-ol derivatives, and enantioselectively convert these alcohols to the corresponding
Silica-Catalysed and Highly Stereoselective Convergent and Nonconvergent Rearrangements of Menthone Enol Acetate Epoxides: Easy Access to the Four α-Hydroxymenthone Stereoisomers
to the biocatalytic access of structurally useful α-hydroxy ketones, we made the unexpected observation that epoxy enolacetates derived from (+)- and (–)-menthone stereoselectivelyrearranged on exposure to silica through a diastereoselective process, providing easyaccess to the complete set of α-hydroxymenthonestereoisomers. The absolute configurations of the fourstereoisomers were unambiguously
The biotransformation of the enantiomeric pairs of 2- and 3-oxygenated p-menthane derivatives with the culturedcells of Nicotianatabacum was investigated. It was found that (i) the culturedcells transform only 2-oxygenated p-menthane derivatives to a great extent, (ii) the culturedcells cause the highly stereospecific reduction for (1R,4R)-2-oxo-p-menthane, whereas this is not the case for its