- Synthesis of Weinreb amides using diboronic acid anhydride-catalyzed dehydrative amidation of carboxylic acids
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The first successful example of the direct synthesis of Weinreb amides using catalytic hydroxy-directed dehydrative amidation of carboxylic acids using the diboronic acid anhydride catalyst is described. The methodology is applicable to the concise syntheses of eight α-hydroxyketone natural products, namely, sattabacin, 4-hydroxy sattabacin, kurasoins A and B, soraphinols A and B, and circumcins B and C.
- Shimada, Naoyuki,Takahashi, Naoya,Ohse, Naoki,Koshizuka, Masayoshi,Makino, Kazuishi
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supporting information
p. 13145 - 13148
(2020/11/09)
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- Antiviral activity of (+)-sattabacin against varicella zoster
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The first report of the antiviral activity of (+)-sattabacin against varicella-zoster virus (VZV) is described. Our results show that (+)-sattabacin potently inhibits the growth of VZV at concentrations in the range of other drugs commonly prescribed for VZV infection. Experiments detailing the synthesis of (+)-sattabacin, quantification of cytotoxicity and gene expression data in human fibroblast cells are also presented. Gene expression data was obtained through microarray analysis from human fibroblast cells exposed to sattabacin in order to identify a possible mechanism by which (+)-sattabacin inhibits VZV replication.
- Mancha, Serena R.,Regnery, Christopher M.,Dahlke, Joshua R.,Miller, Kenneth A.,Blake, David J.
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supporting information
p. 562 - 564
(2013/02/25)
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- Concise, protecting group free total syntheses of (+)-sattabacin and (+)-4-hydroxysattabacin
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The first asymmetric total syntheses of the antiviral natural products (+)-sattabacin and (+)-4-hydroxysattabacin are reported. Both total syntheses are remarkably concise and were completed without the use of protecting groups. These syntheses allowed the unambiguous assignment of the absolute configuration of both natural products. The syntheses of these natural products, which exhibit marked antiviral activity, are readily amenable to the preparation of structural analogs and progress in this regard is also reported.
- Aronoff, Matthew R.,Bourjaily, Neil A.,Miller, Kenneth A.
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supporting information; experimental part
p. 6375 - 6377
(2011/01/03)
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