Process for the production of epothilones and intermediate products within the process
AssigneeNovartis AG
InventorsDieter Schinzer, Anja Limberg, Oliver M. Bohm, Armin Bauer, Martin Cordes
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Abstract
The invention relates to a process for the production of epothilones and intermediate products within the process. Epothilones A and B are natural substances, which can be produced by microorganisms, and the taxols have similar properties and are thus of particular interest in pharmaceutical chemistry.
Claims2
A process for the production of epothilone A or B of formula 1 ##STR43## in which R is hydrogen (A) or a methyl group (B), comprising esterifying a thiazole alkyldiene-alcohol compound of formula 4 ##STR44## with a carboxylic acid of formula 9a ##STR45## in which each B is independently benzyl, tetrahydropyranyl or a silyl protective group, and R is hydrogen or methyl,
- cyclizing the resultant ester by olefin metathesis in the presence of a noble metal catalyst, optionally cleaving the protective groups, epoxidizing the double bond that is newly produced, and optionally cleaving the protective groups.
A deoxy-epothilone of formula 19a ##STR46## wherein R is hydrogen or methyl, and each B' is, independently, benzyl, p-methoxybenzyl, tetrahydropyranyl or a silyl protective group.
Dependencies are inferred from the claim text.