NZYLOXYPHENYL)2,3-BIS(4-METHOXYPHENYL)CYCLOPROPANE - THE SYNTHESIS AND ENANTIOMERIC SEPARATION OF AN ANTITUMOR AGENT

zyloxyphenyl)-2,3-bis(4-methoxyphenyl)cyclopropane (5), a potential an titumor agent designed to treat breast cancer; was prepared in three s teps. A stereospecific palladium-catalyzed cross coupling reaction whi ch provided the intermediate (Z)-triaryl alkene 4 was a crucial step i n the synthesis. Makosza phase transfer reaction on 4 gave the enantio meric (Z)-dichlorocyclopropane derivatives 5 which were resolved by se mipreparative HPLC on a chiral stationary phase consisting of amylose tris-3,5-dimethylphenyl carbamate coated on silica gel. (C) 1994 Wiley -Liss, Inc.