Synthesis of podophyllotoxin derivatives
OwnerJeffrey Sterling, Abraham Nudelman +3inventors
InventorsJeffrey Sterling, Abraham Nudelman, Jaacov Herzig, Ehud Keinan, Ben Z. Weiner
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Abstract
There is provided a novel process for the production of the epipodophyllotoxin glycosides, Etoposide and Teniposide. There are further provided certain novel 4'-demethylepipodophyllotoxin derivatives of the following formula ##STR1## where W is hydrogen or 2,3-di-O-acetyl-4,6,O-ethylidene-D-glucopyran-1-yl. These intermediates are easily transformed into Etoposide and Teniposide and into further derivatives of this series.
Claims9
A process for the production of podophyllotoxin derivatives of formula III ##STR10## which comprises reacting a molar excess of a glucose derivative of formula I ##STR11## with a 4,'-demethylpipodphyllotoxin derivative of formula II ##STR12## in a chlorinated hydrocarbon solvent in the presence of boron trifluoride at a temperature in the range of from -20.degree. C. to 25.degree. C., where:
- T designates tri-lower-alkyl tin,
- A designates alkanoyl or chloroalkanoyl of 1 to 5 carbon atoms, and
- E is identical with A, or both E groups together designate an ethylidene group.
Dependencies are inferred from the claim text.