Synthesis of (2 R ,3 S )-isobutyl phenylisoserinate, the Taxol ® side chain, from ethyl benzoylacetate

Autor:	Peter G. M. Wuts, Rui Lin Gu, Jill M. Northuis
Rok vydání:	2000
Předmět:	biology Organic Chemistry Epoxide Borohydride Medicinal chemistry Catalysis Inorganic Chemistry Potassium carbonate chemistry.chemical_compound Aminolysis chemistry Amide Side chain biology.protein Organic chemistry Amine gas treating Physical and Theoretical Chemistry Lipase
Zdroj:	Tetrahedron: Asymmetry. 11:2117-2123
ISSN:	0957-4166
DOI:	10.1016/s0957-4166(00)00172-5
Popis:	Reduction of ethyl 2-chloro-3-phenyl-3-oxopropionate with borohydride affords predominately the syn -chlorohydrin. Resolution of this ester with the lipase MAP-10 gives (2 S ,3 R )-2-chloro-3-hydroxypropionic acid which after esterification with MeOH/HCl is converted to the cis -epoxide with potassium carbonate and DMF. Aminolysis of the epoxide with aqueous ammonia results in ring opening and amide formation. The amide is converted to an ester upon treatment with isobutyl alcohol and HCl(g) at 100°C. Neutralization then affords the Taxol ® side chain as the free amine.
Databáze:	OpenAIRE
Externí odkaz:	https://explore.openaire.eu/search/publication?articleId=doi_________::316d407fe56d7134950bc42189470688 https://doi.org/10.1016/s0957-4166(00)00172-5 Zobrazit plný text záznamu Full Text from ScienceDirect