Enantioselective synthesis of the complex rocaglate (-)-silvestrol
The total synthesis of the natural product (-)-silvestrol (1) has been accomplished and features enantioselective [3+2] photocycloaddition of a substituted 3-hydroxyflavone and methyl cinnamate promoted by a chiral Bronsted acid. Initial biological studies indicate a 5-10-fold greater activity of silvestrol as an inhibitor of protein synthesis in HeLa cells than its 1″″ diastereomer.
Gerard, Baudouin,Cencic, Regina,Pelletier, Jerry,Porco Jr., John A.
p. 7831 - 7834
(2008/09/19)
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