Process for the synthesis of 3',4'-anhydrovinblastine,...

Details Process for the synthesis of 3',4'-anhydrovinblastine,... Process for the synthesis of 3',4'-anhydrovinblastine,...

C - Chemistry, Metallurgy

07

D

260/237.3

C07D 519/04 (2006.01)

Patent

CA 1341261

A process for the synthesis of bisindole alkaloids of the vinblastine and vincristine family from an indole unit, such as catharanthine, and a dihydroindole unit, such as vindoline, wherein conversion of an initially-formed dimeric iminium intermediate to an enamine is achieved by a novel 1,4-reduction method employing various 1,4-dihydropyridine compounds. The resulting enamine can be transformed to a second iminium intermediate by controlled aeration and oxidation in the presence of various oxidizing reagents. The second iminium intermediate is then reduced with alkali metal boro- hydride to produce the target compound vinblastine or vincristine. The entire process can be conducted in a one-pot operation to obtain the target product without isolation of the intermediates.

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