Tetrahedron letters

A four-step synthesis of erythro-m-chloro-3-hydroxytyrosine ethyl ester enantiomerically pure

A Solladié-Cavallo, T Nsenda

Index: Solladie-Cavallo, Arlette; Nsenda, Thomas Tetrahedron Letters, 1998 , vol. 39, # 15 p. 2191 - 2194

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Citation Number: 12

Abstract

Pure erythro-m-chloro-3-hydroxytyrosine having the (2R, 3R)) configuration, a residue of Vancomycin and Aridicin A, has been prepared in 4 steps using an aldol addition involving a directly generated titanium enolate derived from a chiral iminoglycinate.(+)- Hydroxypinanone was used as a recoverable chiral auxiliary. The (2S, 3S)-erythro isomer will be, of course, available from (−)-hydroxypinanone.

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