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AssigneeThe Scripps Research Institute
InventorsSubhash C. Sinha, Richard A. Lerner, Carlos F. Barbas, III
Estimating the term…
Three monoclonal aldolase antibodies, generated against a β-diketone hapten by reactive immunization, catalyzed rapid and highly enantioselective retro-aldol reactions providing ent-9a-k by kinetic resolution. Compounds 9a, 9g and 9k were resolved in multi-gram quantities using 0.005-0.0004 mol % antibody catalyst. Enantiomerically pure starting materials, 9a-k, are useful synthons for the construction of epothilones A-E (2-6) and their analogs including 13-alkyl derivatives. Previously, the use of compound 9a as a synthon was reported in the preparation of epothilones A-D, 2-5. To further expand this synthon-based strategy, syntheses of epothilone E, 6, 13-methyl epothilone C, 7, and their trans-isomers have been achieved starting from enantiomerically pure thiazole aldols 9g and 9a, respectively, prepared by large-scale antibody catalyzed resolutions.
A process for enantioselectively resolving a racemic mixture of an aldol synthon, the racemic mixture including a first and a second enantiomer of the aldol synthon, said process comprising the following steps:
A process for enantioselectively resolving a racemic aldol synthon, the racemic aldol synthon including a first and a second enantiomer, said process comprising the following steps:
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