A process for the preparation of demethylepypodophyllotoxin

Details A process for the preparation of demethylepypodophyllotoxin A process for the preparation of demethylepypodophyllotoxin

C - Chemistry, Metallurgy

07

H

C07H 15/26 (2006.01) C07H 13/04 (2006.01) C07H 17/04 (2006.01) C07H 23/00 (2006.01)

Patent

CA 2113894

Disclosed herein is a process for producing novel DMEP-.beta.-D-glucosides of formula (I), wherein R1 is lower alkanoyl group, haloacetyl group, or both R1, taken together, form an alkylidene, arylalkylidene or heteroarylalkylidene group; R2 is lower alkanoyl or haloacetyl group; R4 is hydrogen, characterized in that a compound of formula (III) wherein R4 is hy- drogen, is reacted with a compound of formula (II) wherein R1 is lower alkanoyl group, haloacetyl group, or both R1, taken together, form an alkylidene, arylalkylidene or heteroarylalkylidene group; R2 is lower alkanoyl or haloacetyl group; R3 is hydrogen or trialkylsilyl group, in the presence of a Lewis acid such as boron trifluoride. The compounds of formula (I) thus prepared are valuable intermediates for the production of DMEP-.beta.-D- glucosides including Etoposide (I, both R1= ethylidene, R2 = H, R4 = H) and Teniposide (I, R1 = thenylidene, R2 = H, R4 = H).

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