A NEW APPROACH TO SYNTHESIS OF VINBLASTINE ANALOGS - ADDITION OF ORGANOZINC REAGENTS TO THE DIHYDROPYRIDINIUM ION GENERATED BY FRAGMENTATIVE COUPLING OF CATHARANTHINE AND VINDOLINE

Authors
SUNDBERG RJ BETTIOL JL GADAMASETTI KG MARSHALLA M KELSH L
Citation
Rj. Sundberg et al., A NEW APPROACH TO SYNTHESIS OF VINBLASTINE ANALOGS - ADDITION OF ORGANOZINC REAGENTS TO THE DIHYDROPYRIDINIUM ION GENERATED BY FRAGMENTATIVE COUPLING OF CATHARANTHINE AND VINDOLINE, Bioorganic & medicinal chemistry letters, 4(16), 1994, pp. 1999-2004
Citations number
16
Categorie Soggetti
Chemistry Inorganic & Nuclear","Chemistry Medicinal
Journal title
Bioorganic & medicinal chemistry letters → ACNP
ISSN journal
0960894X
Volume
4
Issue
16
Year of publication
1994
Pages
1999 - 2004
Database
ISI
SICI code
0960-894X(1994)4:16<1999:ANATSO>2.0.ZU;2-S
Abstract
The dihydropyridinium ion generated by Potier-Polonovski coupling of c atharanthine and vindoline reacts with organozinc reagents to give eit her 15' or 21'-substituted adducts. The former are unstable enamines b ut 20'-deoxyvinblastine analogs can be isolated after NaBH4 reduction. 21'-Phenylanhydrovinblastine and the 15'-ethyl, 15'-tert-butyl and 15 '-phenyl analogs of 20'-deoxyvinblastine show activity in the micromol ar range as tubulin assembly inhibitors.