Concise Stereoselective Synthesis of (−)‐Podophyllotoxin by an Intermolecular Iron(III)‐Catalyzed Friedel–Crafts Alkylation | Zendy

Stadler Daniel | Zendy; Bach Thorsten | Zendy

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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.

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