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Concise Stereoselective Synthesis of (−)‐Podophyllotoxin by an Intermolecular Iron(III)‐Catalyzed Friedel–Crafts Alkylation
Author(s) -
Stadler Daniel,
Bach Thorsten
Publication year - 2008
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.200802611
Subject(s) - podophyllotoxin , stereocenter , chemistry , alkylation , natural product , stereochemistry , total synthesis , combinatorial chemistry , organic chemistry , catalysis , enantioselective synthesis
Without further ado , the building blocks 1 – 3 were combined in three CC bond‐forming reactions to provide the enantiomerically pure natural product (−)‐podophyllotoxin ( 4 ). The stereogenic center at C1 was generated in the key reaction, a diastereoselective iron(III)‐catalyzed intermolecular Friedel–Crafts alkylation.