( Z )‐1,1‐dichloro‐2‐(4‐benzyloxyphenyl)‐2,3‐bis(4‐methoxyphenyl)cyclopropane: The synthesis and enantiomeric separation of an antitumor agent | Zendy

Meyer Karen L. | Zendy; Magarian Robert A. | Zendy

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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.

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