Synthesis of (1R,2S)-1-(3'-chloro-4' -methoxyphenyl)-1,2-propanediol (trametol) and (1R,2S)-1-(3',5'-dichloro-4'-methoxyphenyl)-1,2-propanediol, chlorinated fungal metabolites in the natural environment.
(1R,2S)-1-(3'-Chloro-4'-methoxyphenyl)-1,2propanediol (Trametol, 3), a metabolite of the fungus Trametes sp. IVP-F640 and Bjerkandera sp. BOS55, was synthesized by employing Sharpless asymmetric dihydroxylation as the key step. Similarly, the (1R,2S)-isomer of 1-(3',5'-dichloro-4'-methoxyphenyl)-1,2-propanediol (4), another metabolite of Bjerkandera sp. BOS55, was synthesized by asymmetric dihydroxylation.
Kousaka
Takeshi
T
Department of Mathematics and Science Education, Graduate School of Science, Science University of Tokyo, Japan.
Mori
Kenji
K
D001487:Basidiomycota / Q000378:metabolism*; D002733:Chlorophenols / Q000378:metabolism*; D006900:Hydroxylation; D007202:Indicators and Reagents; D009682:Magnetic Resonance Spectroscopy; D011409:Propylene Glycols / Q000138:chemical synthesis* / Q000737:chemistry; D013237:Stereoisomerism
C468187:(1,2)-1-(3'-chloro-4' -methoxyphenyl)-1,2-propanediol; D002733:Chlorophenols; D007202:Indicators and Reagents; D011409:Propylene Glycols