STRUCTURE ELUCIDATION AND SPECTRAL ASSIGNMENT OF ANALOGS OF NAVELBINE(R) (8'-NORANHYDROVINBLASTINE)

During the development of the bis-indole alkaloid anticancer drug Nave lbine(R) (vinorelbine), several chemical degradants of the drug were i solated and identified. These included 7'-nor-6',9'-secovinorelbine (7 ',8'-bisnor-6',9'-secoanhydrovinblas tine) and 4-deacetyl-8'-vinorelbi ne (4-deacetyl-8'-noranhydrovinblastine). The elucidation of the struc ture of 7'-nor-6',9'-secovinorelbine is described; the assignment of t he proton and carbon spectra of both compounds is contrasted to the sh ift assignments of Navelbine.