Synthesis of pancratistatin

Details Synthesis of pancratistatin Synthesis of pancratistatin

2005-09-27

2005-09-27

Aulakh, Charanjit S. (Department: 1625)

Organic compounds -- part of the class 532-570 series

Organic compounds

Heterocyclic carbon compounds containing a hetero ring...

C546S061000, C546S062000

Reexamination Certificate

active

06949647

ABSTRACT:
(+)-Narciclasine (2), available in quantity from certainAmaryllidaceaespecies or by total synthesis, is employed in for a ten step synthetic conversion (3.6% overall yield) to natural (+)-pancratistatin (1a). The key procedures involve the epoxidation of natural (+)-narciclasine (2) to an epoxide (6), reduction of the epoxide (6) to diol (8), formation of cyclic sulfate (12) and its ring opening with cesium benzoate followed by saponification of the benzoate to afford (+)-pancratistatin (1a).

REFERENCES:
patent: 5529989 (1996-06-01), Pettit et al.
Pettit, G.R. et al.: Synthesis of 10b-R-hydroxy-pancratistatin via narciclasine. J. Chem. Soc. Chem. Commun. pp. 2725-2726, 1994.
Pettit, G.R. et al.: Antineoplastic agents.450.Synthesis of (+)-Pancratistatin from (+)-Narciclasine as relay. J. Org. Chem. vol. 66, pp. 2583-2587, 2001.

Affiliated with

Also associated with

Rating

Synthesis of pancratistatin does not yet have a rating. At this time, there are no reviews or comments for this patent.

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

Rate now

Comments { 0 }

Profile ID: LFUS-PAI-O-3410033