Process of synthesis of 3',4'-anhydrovinblastine, vinblastine and vincristine
USRE37449E · kind E · reissue
Assignee
Inventors
Key dates
| Filing date | Nov 10, 1999 |
| Grant date | Nov 13, 2001 |
| Priority date | — |
| Expiry date | Nov 10, 2019 |
Classification
- Technology area (CPC —)General
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.