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Enantioselective Synthesis of the Complex Rocaglate (−)‐Silvestrol
Author(s) -
Gerard Baudouin,
Cencic Regina,
Pelletier Jerry,
Porco John A.
Publication year - 2007
Publication title -
angewandte chemie international edition
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 5.831
H-Index - 550
eISSN - 1521-3773
pISSN - 1433-7851
DOI - 10.1002/anie.200702707
Subject(s) - enantioselective synthesis , natural product , hela , stereochemistry , diastereomer , chemistry , total synthesis , biochemistry , catalysis , cell
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 Brønsted 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.