Process of synthesis of vinblastine and vincristine

Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...

Patent

Rate now

  [ 0.00 ] – not rated yet Voters 0   Comments 0

Details

540479, 546 51, C07D51904

Patent

active

050475282

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.

REFERENCES:
patent: 4144237 (1979-03-01), Kutney
patent: 4199505 (1980-04-01), Szantay et al.
patent: 4279817 (1981-07-01), Kutney
patent: 4305875 (1981-12-01), Potier et al.
patent: 4737586 (1988-04-01), Potier et al.
patent: 4778885 (1988-10-01), Vukovic et al.
patent: 4841045 (1989-06-01), Kuehne
Kutney, et al., Helvetica Chimica Acta, vol. 59, No. 8, pp. 2858-2882 (1976).
Fieser, et al., "Reagents for Organic Synthesis", vol. 6, Wiley-Interscience, John Wiley & Sons, New York, 1987, pp. 36-37.
Nishiyama, et al., Chemical Abstracts, vol. 84: 179294h (1976).
Nakumura, et al., Chemical Abstracts, vol. 101: 229474j (1984).
Langlois, et al., Tetrahedron Letters, No. 14, pp. 1099-1102 (1976).
Mangeny, et al., J. Am. Chem. Soc., vol. 101(8), p. 2243-2245 (1979).
Kutney, et al., Heterocycles, vol. 27(8), pp. 1845-1853 (08/88).

LandOfFree

Say what you really think

Search LandOfFree.com for the USA inventors and patents. Rate them and share your experience with other people.

Rating

Process of synthesis of vinblastine and vincristine does not yet have a rating. At this time, there are no reviews or comments for this patent.

If you have personal experience with Process of synthesis of vinblastine and vincristine, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process of synthesis of vinblastine and vincristine will most certainly appreciate the feedback.

Rate now

     

Profile ID: LFUS-PAI-O-541072

  Search
All data on this website is collected from public sources. Our data reflects the most accurate information available at the time of publication.