- 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
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(1R,2S)-1-(3′-Chloro-4′-methoxyphenyl)-1,2-propanediol (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,Mori, Kenji
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p. 697 - 701
(2007/10/03)
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- Identification and synthesis of novel chlorinated p-anisylpropanoid metabolites from Bjerkandera species
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Analysis of the EtOAc extracts from the culture medium of Bjerkandera sp. BOS55 and B. fumosa revealed the presence of two novel chlorinated metabolites. Their structures were unambiguously established as erythro-1- (3',5'-dichloro-4'-methoxyphenyl)-1,2-propanediol (2) and 1-(3'-chloro-4'- methoxyphenyl)-3-hydroxy-1-propanone (3) through synthesis of authentic samples and comparison of retention times and mass spectral data. The production of trametol (1) by Bjerkandera sp, BOS55 was also a new finding.
- Swarts, Henk J.,Verhagen, Frank J. M.,Field, Jim A.,Wijnberg, Joannes B. P. A.
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p. 1110 - 1114
(2007/10/03)
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