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Catalytic Asymmetric Total Synthesis of ent ‐Hyperforin
Author(s) -
Shimizu Yohei,
Shi ShiLiang,
Usuda Hiroyuki,
Kanai Motomu,
Shibasaki Masakatsu
Publication year - 2010
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.200906678
Subject(s) - hyperforin , chemistry , enantioselective synthesis , total synthesis , stereochemistry , kinetic resolution , hypericum perforatum , bicyclic molecule , histone deacetylase , biomimetic synthesis , desymmetrization , aldol reaction , combinatorial chemistry , intramolecular force , catalysis , organic chemistry , histone , biochemistry , biology , dna , pharmacology
Key to success : The first catalytic asymmetric total synthesis of ent‐ hyperforin (see picture) was accomplished by using a Diels–Alder reaction promoted by a chiral cationic iron catalyst ( A ; 96 % ee , d.r.>33:1), a diastereoselective Claisen rearrangement ( B ; 12:1 selectivity), an intramolecular aldol reaction ( C ), and a vinylogous Pummerer rearrangement ( D ) as key steps.
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