(Z)‐1,1‐dichloro‐2‐(4‐benzyloxyphenyl)‐2,3‐bis(4‐methoxyphenyl)cyclopropane: The synthesis and enantiomeric separation of an antitumor agent
作者:
Karen L. Meyer,
Robert A. Magarian,
期刊:
Chirality
(WILEY Available online 1994)
卷期:
Volume 6,
issue 1
页码: 41-45
ISSN:0899-0042
年代: 1994
DOI:10.1002/chir.530060108
出版商: Alan R. Liss, Inc.
关键词: chiral HPLC;Chiralpak AD;amylose carbamate stationary phase;antiestrogen;breast cancer;dichlorotriarylcyclopropane
数据来源: WILEY
摘要:
Abstract(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 alkene4was a crucial step in the synthesis. Makosza phase transfer reaction on4gave the enantiomeric (Z)‐dichlorocyclopropane derivatives5which were resolved by semipreparative HPLC on a chiral stationary phase consisting of amylose tris‐3,5‐dimethylphenyl carbamate coated on silica ge
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