Process of synthesis of vinblastine and vincristine
US5047528A · kind A · utility
Assignee
Inventors
Key dates
| Filing date | Aug 2, 1988 |
| Grant date | Sep 10, 1991 |
| Priority date | — |
| Expiry date | Aug 2, 2008 |
Classification
- Technology area (CPC C)Chemistry; Metallurgy
- CPC primaryC07D519/04
- WIPO fieldOrganic fine chemistry
- WIPO sectorChemistry
Abstract
The present invention relates to the synthesis of dimer alkaloid compounds, particularly those of the Catharantus (Vinca) family, from an indole unit, such as cantharanthine, and a dihydroindole unit, such as vindoline. A multi-step process is disclosed including the steps of (1) of 1,4-reduction of a first dimeric iminium intermediate to an enamine compound by reaction with a 1,4-dihydropyridine compound; (2) oxidative transformation of the resulting enamine to a second iminium intermediate under controlled aeration; (3) reduction of the second iminium intermediate to form the target dimer alkaloid compounds. The entire process can be conducted in a one-pot operation to obtain the target compounds without isolation of the intermediates.
Source: USPTO / EPO open patent data. Objective bibliographic and citation counts.