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( Z )‐1,1‐dichloro‐2‐(4‐benzyloxyphenyl)‐2,3‐bis(4‐methoxyphenyl)cyclopropane: The synthesis and enantiomeric separation of an antitumor agent
Author(s) -
Meyer Karen L.,
Magarian Robert A.
Publication year - 1994
Publication title -
chirality
Language(s) - English
Resource type - Journals
SCImago Journal Rank - 0.43
H-Index - 77
eISSN - 1520-636X
pISSN - 0899-0042
DOI - 10.1002/chir.530060108
Subject(s) - chemistry , cyclopropane , enantiomer , stereospecificity , silica gel , alkene , cyclopropanation , chiral column chromatography , catalysis , stereochemistry , medicinal chemistry , organic chemistry , ring (chemistry)
( Z )‐1,1‐Dichloro‐2‐(4‐benzyloxyphenyl)‐2,3‐bis(4‐methoxyphenyl)cyclopropane ( 5 ), a potential antitumor agent designed to treat breast cancer, was prepared in three steps. A stereospecific palladium‐catalyzed cross coupling reaction which provided the intermediate ( Z )‐triaryl alkene 4 was a crucial step in the synthesis. Makosza phase transfer reaction on 4 gave the enantiomeric ( Z )‐dichlorocyclopropane derivatives 5 which were resolved by semipreparative HPLC on a chiral stationary phase consisting of amylose tris‐3,5‐dimethylphenyl carbamate coated on silica gel. © 1994 Wiley‐Liss, Inc.