Process for the preparation of combretastatins

1. Field of the Invention The present invention provides novel processes for the preparation of combretastatins or stilbene compounds of formulae (I) and (III) wherein A is NHor and PG is a protecting group.The disclosed and claimed processes include (1) Wittig condensation between a nitromethoxyben...

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Bibliographic Details
Main Authors Mutti, Stéphane, Lavigne, Michel, Malejonock, Irina, Casimir, Jean-Paul
Format Patent
LanguageEnglish
Published 06.07.2004
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Summary:1. Field of the Invention The present invention provides novel processes for the preparation of combretastatins or stilbene compounds of formulae (I) and (III) wherein A is NHor and PG is a protecting group.The disclosed and claimed processes include (1) Wittig condensation between a nitromethoxybenzaldehyde and a trimethoxybenzylphosphonium salt or between a trimethoxybenzaldehyde and a nitromethoxybenzylphosphonium salt to provide an intermediate compound of formula (I) wherein A is NO, and subsequent iron powder reduction to provide a compound of formula (I) wherein A is NH; (2) Wittig condensation of the same precursor aldehydes and phosphonium salts wherein NOis replaced by NHto provide a compound of formula (I) wherein A is NH; and (3) a process for condensation of a compound of formula (I) wherein A is NHwith a doubly protected serinamide to provide an intermediate of formula (III), and subsequent hydrolysis to provide a compound of formula (I) wherein A is -NH-C( O)CH(NH)CHOH, or the pharmaceutically acceptable salts thereof. Also claimed is a compound of formula (III).